


Breaking Dean

by BottomDean67



Category: Supernatural
Genre: Anal Sex, Bottom Dean Winchester, Bottom Dean Winchester/Top Sam Winchester, Chastity Device, Cock Cages, Come Swallowing, Demons, Dildos, Eventual Dean Winchester/Sam Winchester, Eventual Romance, Evil Sam Winchester, Fucking Machines, Gags, Glory Hole, Hurt Dean Winchester, Latex, M/M, Nipple Play, Non-Consensual Bondage, Plot Twists, Rape/Non-con Elements, Rough Oral Sex, Scared Dean Winchester, Smut, Wincest - Freeform, eventual Happy relationship, eventual happy dean
Language: English
Status: In-Progress
Published: 2019-02-24
Updated: 2019-02-24
Packaged: 2019-11-05 04:37:24
Rating: Explicit
Warnings: Rape/Non-Con
Chapters: 11
Words: 25,176
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/17912147
Author URL: https://archiveofourown.org/users/BottomDean67/pseuds/BottomDean67
Summary: Dean hasn't seen Sam in years, not since he became the ruler of Hell. But Sam's back and unfortunately for Dean, Sam seems only focused on turning Dean into his own personal sex toy. Will Dean be able to survive everything Sam throws at him? Or will Dean lose himself and give Sam exactly what he wants?





	1. Chapter 1

**Author's Note:**

> A/N: I decided to repost this story and change a few of the tags on it after going back and adding more to it. I was never happy with where I originally ended it and had more written so I decided to change things up and start to explore that side of things as well. It's still on going so I will try to update regularly.
> 
> This is a DARK fic with non-con elements, evil Sam, and Dean does not have a good time for awhile. If this bothers you, please do not read. 
> 
> There will eventually be some happiness (it'll take a while and trust me on it) but I like the story better by adding that other part into it and hopefully ya'll will too.

“Rise and shine, pretty boy,” Dean heard. He groggily opened his eyes, hazy at first but fully awake when he realized he was looking at Sam. So much of him was the same. Sam still wore flannel, a dark red one that was buttoned up with rolled up sleeves, relaxed jeans and boots. For a moment he looked like the little brother Dean remembered losing. The Sam that went to hell to take over, to make things better. Dean had noticed in the three years Sam had been gone that things had gotten considerably better on the hunting side of things. But Dean was truly alone in the world now and he had never grown used to it.

“Mphf hmf,” Dean mumbled as Sam ran a few fingers through his hair, coughing when he realized he was gagged and something had been forcibly shoved in his mouth before he was woke. He tried to spit it out, tongue curling over the round tip of whatever it was. It was cylindrical and had a few strange lines to it as Dean tried to figure out what it was, Dean shaking his head as he attempted to rid the object from his mouth.

“Ah, ah,” said Sam with a smirk, patting Dean’s cheek so he could feel the leather straps pressing into the skin of his face, wrapped and secured around the back of his head to keep the object from being removed. “That penis gag is staying in for a good long while.”

“Mhfm hm!” Dean tried to shout back at Sam, wincing now that he realized that was  _ exactly _ the shape of the thing in his mouth. He flexed his hands, finding they were chained above his head in leather cuffs and some strange mittens were covering them, rendering his hands useless. He looked around, spotting he was in the dungeon of the bunker, swallowing hard and trying to ignore the fake penis in his mouth. He felt cool and realized he was naked, his feet barely touching the floor from where they too were cuffed down and secured. Dean gave a good thrash of his body and didn’t even budge an inch.

“If you’re done realizing you aren’t going anywhere, can we move on, sweetheart?” said Sam. Dean glared at him, his true little brother long gone. Whatever this version of him was, it was not the sweet Sam he knew. 

Dean’s eyes followed Sam over to the table in the corner of the room, wide when he saw what was laid out on top of it.

“Excited? I know I am,” said Sam, picking two objects up. He stalked over to Dean like he was sizing up his prey, Dean’s body betraying him when it flushed pink at the thought of being naked while Sam was fully clothed.

Sam held the objects up in front of Dean, Dean staring at him, his breath coming quickly.

“Calm down, sweetie. I know you want them on,” said Sam. He reached down with his free hand and picked up Dean’s soft cock, Dean jerking at the contact of Sam’s cool hand. “Sorry. I guess you’ll get used to that in time.”

Dean didn’t have the focus to think about what  _ that _ meant because Sam was holding up a thin metal rod and lubing it up. Sam held Dean’s cock in his hand as he lined up the sound with Dean’s tip and slowly inserted it. Dean tried to move away but he had nowhere to go, Sam tsking him until the tip of it was pressed against the head of his cock. 

“You’ll hurt yourself if you keep that up. Actually you would have had I not made some wonderful improvements to that gorgeously slutty body of yours while you were sleeping,” said Sam. Dean tried to shout as Sam took hold of the other object now, a metal cock cage and nestled it around Dean’s cock. Sam gave Dean’s cock a few good pumps for the hell of it, smiling darkly before the cage slipped into place, digging into Dean’s cock as it tried to get hard from the contact of Sam’s hand. 

Sam muttered something and Dean watched in horror as the lock on the cage disappeared, keeping the sound and cage in place.

“Oh, that won’t ever be coming off. You’ll never be coming again. Didn’t I mention that?” said Sam, laughing as he walked back to the table. Dean squeezed his eyes shut, his body sticky with sweat already as he tried to keep calm and not think about that. If he could get out, he just had to get to the door and could lock Sam in the dungeon while he figure out a plan. Dean glanced up at his hands in the mittens, eyes wide when he saw the cuffs no longer had adjustments on them, the mittens seemingly strapped in place under them magically.

Sam was already halfway back to him, holding up a leather band that had Dean confused until Sam was lifting Dean’s cock up and out of the way.

“A cock ring for the boy,” said Sam, securing it tightly in place, Dean letting out a low hiss. Sam dug into his back pocket and pulled out another kind of band, placing it over the cock ring so it was squeezing him hard. “You’ll only need to wear that one for a few days before we put on the tighter one.”

_ Tighter one?  _ Dean’s balls already felt like they were going to burst, Dean groaning lowly. 

“Eh, it won’t do any damage. Might as well put it on now,” said Sam, Dean shaking his head vigorously as Sam put on another band on top of what was already there, Dean whimpering when it pain shot through his balls. “That stays on until those ugly little things fall off. You won’t feel anything soon.”

Dean couldn’t believe what he was hearing, Sam standing in front of him with a smile.

“That’s a castration band. You won’t be coming anymore so we have no need for those nasty things or your nasty cum,” said Sam. “Don’t worry. They’ll be gone in a week or so and then you’ll be nice and bare.”

Sam tapped the underside of Dean’s cock, fingertips grazing his throbbing balls, Dean letting out a sob at the intense pain.

“Aw, don’t cry yet, Dean. I want to get into some proper training before you start with the water works,” said Sam. Dean glared at Sam, not moving a muscle until his mouth was filled with saliva and he was forced to swallow, gentle suckling the fake head in his mouth at the motion. “You’re going to be such a good toy for me.”

Dean would have spit at him if he could have but Sam was picking up the last two objects on the table, Dean throwing his head back when he saw what they were. He shrieked when he felt cold metal on his nipple, looking down in time to see Sam attach the other nipple clamp to his swollen buds. Sam smiled as he adjusted the tightness of them, Dean’s nipples turning a deep red as the pain pulsated from them.

“Such sensitive nipples,” teased Sam, flicking them each once, earning a sharp howl from Dean. He walked around Dean’s backside, trailing a finger down his spine and pulling a shiver from Dean. “You have a great ass Dean. I can’t wait to take it.”

Dean tried to get out of his bonds again but failed, body stilling when he felt a cool wet finger at his backside, running over his rim a few times.

“Your hole is so tiny,” said Sam, pressing up against Dean’s back, wrapping an arm across Dean’s chest, pressing the clamps in harder, Dean wailing into his gag. “Just think. After today, your hole is never going to be this tiny ever again. I know what a slut you are for something stuffing that hole of yours, Dean.”

Sam pressed a slick finger inside, up to the knuckle, pumping it in and out a few times before adding a second and scissoring Dean open.

“We’re gonna keep you stuffed 24/7 like a good boy should be,” said Sam, crooking his fingers until he found Dean’s prostate. Dean moaned at the sharp jolt of pleasure and then jerked when his cock couldn’t get hard, Sam laughing behind him. “I got what you need baby. One more minute.”

Sam worked Dean open only a bit more. He wanted a tight fit and Dean to feel it after all. Sam slicked lube up over the thick plug before he pressed it to the tip of Dean’s hole, pushing it in with some resistance from Dean’s body, making sure Dean got to feel the full stretch of the widest part for a good long minute before he pushed it inside.

Dean moaned as the plug settled itself inside and he tightened up around it, feeling the fullness of it, but he managed to cut himself off, flexing his arms as he tried to free himself. Sam could see he was already starting to understand he lost the fight the second he woke up in here.

Sam owned him. It was only a matter of time before Dean realized that and grew to love being nothing more than Sam’s toy.

“You look so pretty all caged and stuffed like that, big brother,” said Sam, Dean glaring at him, a hint of water in them betraying him. “I didn’t hurt your little hole did I? It’ll be trained up soon enough. You’ll be so open and loose back there, you won’t settle for anything less than the size of my fist.”

Dean blinked away his tears, snarling as best he could at Sam.

“Now’s the time I should tell you about those improvements I made. See, I know you’re thinking you’ll break out when you need to take care of some human functions. But see, with me being head demon and all, I know of some pretty, pretty interesting magic now. Magic I used on you. Magic like...you don’t need to eat food anymore. Or need water. No bathroom necessary either. You won’t die. Not unless I let you and big brother, I’m never letting that happen,” said Sam.

Dean stared at Sam’s dark lust filled eyes, horrified when he knew Sam wasn’t lying. He could leave him trussed up like forever if you wanted and there was no way out. 

“Once you’re good and trained, you won’t even miss your burgers or pie. All you’ll want is some of your favorite yummy snack. You don’t need it but good boys drink it up because they’re little cum sluts,” said Sam. He headed out of the room and returned a few minutes later with a small white bag and a thin plastic tube. “I heated it up for you. I got plenty where this came from but let’s start you off with one for now. You’ve had a rough day after all.”

Dean watched Sam put a hand on his gag, doing something to the end of it before he started to feed the tube into what Dean guessed was a slot. He never felt it poke into his mouth but Same quickly stopped and attached the bag to the chains above Dean’s head. Dean immediately felt a salty liquid fill his mouth through the tip of the penis gag, Dean trying to shout at the intrusion as it filled his mouth.

“Swallow or you’ll choke,” said Sam. Dean tried to block the tip with his tongue but it was no use, Sam’s cum flowing freely into his mouth, forcing Dean to swallow it down as more dripped down. “Good boy. I can tell you like that. I’ll slow down the tap some. You can snack on that for the next fifteen minutes. Tomorrow I’ll give you a full bag.”

Dean couldn’t stop the tears that fell down his face, Sam shushing him as Dean felt the stream slow to something more manageable, Sam cupping Dean’s cheek as Dean started to suckle the cock head when he realized that made it go down easier.

“You suck that cock real good, Dean,” said Sam, kissing Dean’s forehead. “I’m so proud of you. You’re going to be the best toy I’ve ever had and you know what? You’re going to be happier than you’ve ever been just being my cumdump and fuck toy. I promise.”

Dean whined as he swallowed down another load of Sam’s cum, Sam chuckling to himself.

“I have some business to attend to and you need to get antiquated with how things work now. I’ll come back tomorrow, baby boy.”

Dean shouted as Sam left the room and flicked off the lights, leaving Dean alone in the dark, cock caged and filled with a sound, balls bound, ass stuffed, nipples ready to burst and mouth suckling on a fake cock that was force feeding him his brother’s cum.

He was fucked.


	2. Chapter 2

Dean realized he could still sleep hours after Sam had left. It was horribly uncomfortable to sleep practically standing in the chains and he only got snippets of meaningful rest through the pain but when he finally opened his eyes again, he felt okay. Not tired, not fully awake. Just okay.

There was no urge for food, no need to use a bathroom, no thirst that made it’s way to him. Dean wasn’t sure to be mortified or grateful when the pain in his balls began to diminish and then stopped altogether. Sam was all evil now, something demonic about him but not quite a demon. 

Dean thought he was far worse than one of those.

Dean tried to shift on his feet, reminded of the sore fullness of his ass and the pain in his nipples. He shouted at the sudden sensation, muffled into barely more than a incoherent soft noise around the penis gag. He hadn’t even realized he’d been sucking on it absently for the past ten minutes or so. His eyes felt hot but Dean knew he had to keep it together if he was going to get out. He had to.

 

“Hello, toy,” said Sam, flicking on the bright light, Dean opening his eyes as he saw Sam carrying in a new, much bigger bag. He set it down on the table and removed the old one from where he’d hung it the day before, Sam brushing his thumb across Dean’s cheek as he did so. “S’okay if you cry. I like it when you do.”

Dean thought about saying something smart back but Sam would never hear it and behaving was the only way he saw himself getting out of this room. Dean blinked and gave a small nod of his head, a pleased smile crossing Sam’s lips.

“Good boy. You’ve always been so smart,” said Sam. He stared at Dean and snapped his fingers, Dean suddenly on his knees on the floor, hands behind his back. He groaned at the change in position, cramping for a moment before his body relaxed and Sam was carding fingers through Dean’s hair.

Dean nearly cried when Sam reached around and undid the penis gag, pulling it from Dean’s mouth and placing it aside. Dean coughed and his jaw ached but Sam quickly had a hand under his chin, grasping it roughly.

“Sammy. Lemme go,” said Dean quietly, Sam running his finger over Dean’s plump lips. “I won’t do anything. You can run hell. I’ll never hunt again. Let me go and we’ll forget this ever happened.”

“Tempting. Not,” said Sam, forcing his lips against Dean’s, Dean trying to pull away until Sam’s hands forced his head in place and Dean had to take it. “Open that mouth of yours and if you bite, I’ll fuck you raw.”

Dean whimpered and involuntarily clenched around the plug in his ass, knowing how sore he already felt and that a cock as sure as Sam was bound to have going in him dry would wreck him.

Dean let his lips part as tears streamed down his eyes, Sam’s tongue invading his mouth with a bruising force, Sam moaning into Dean, stealing his breath away. Dean sat there and took it, whining when Sam let a finger trail down his chest and he played with the nipple clamps.

“So fucking hot for it, aren’t you?” said Sam, leaning back, holding the back of Dean’s neck as one hand teased his nipples.

“No,” said Dean, turning his head away. Sam fingered the clamps on Dean’s nipples for a moment before he released them. Dean hissed as the blood rushed back to them only to feel the clamps secure back on, tighter than before if that were possible. “Sam!”

“Good toys are quiet,” said Sam, giving Dean a chaste kiss before he stood up and pulled down his pants. A hard cock popped out, Sam rubbing the tip of his monstrous length against Dean’s lips and smearing precome over them. “Time to suck the real thing, toy.”

Dean shook his head but his lips parted when Sam squeezed his jaw, forcing his cock inside. Dean gagged as it hit the back of his throat, Sam chuckling when he pulled back a bit and he forced Dean to look up at him.

“Those lips stretched around my cock...I can’t wait to see your puffy red rim around it,” said Sam, fisting a hand in the back of Dean’s hair and slamming his length in. Dean swallowed around him and continued to gag, Sam pulling back out and repeating it over and over again until Dean got a hang of how to breath. “Learning how to deep throat like a good toy. I might not fuck you raw after all.”

Dean whimpered as he remembered the threat, tears prickling in his eyes at how roughly Sam was using his throat. He could feel it when Sam’s cock started to twitch and swell, Sam’s hands forcing Dean to take him the whole way, cock down Dean’s throat as Sam started to come.

“Swallow,” said Sam. “Work my cock with your throat.”

It wasn’t hard to do with the fact Dean couldn’t breathe, his throat constricting around Sam’s length, earning a fresh spurt of come down his throat, sliding down until Dean felt it pool in his stomach. Sam kept emptying his come until Dean felt like he was going to pass out, Sam finally pulling out and Dean sagging down to the floor.

“You did such a good job with that, toy, I think you deserve a step up in your training,” said Sam. Dean barely managed to lift his head when he saw Sam with the penis gag in his hand but this one was wide and looked like it was a little longer.

Dean shouted as it was shoved in his mouth, stretching his lips wide around the base, the tip of resting further back in his mouth so the only comfortable position was to suckle it. 

“Time for your cum dump,” said Sam, snapping his fingers, Dean back in a standing position, the white bag Sam had brought in hung up above him and a thin tube leading it down to the gag. He fiddled with something on the bag and Dean felt the quick, steady stream of cum fill his mouth again, Dean swallowing it down easier this time. “Such a good boy drinking his cum, aren’t you?”

Sam rested a hand on Dean’s throat, feeling each and every one of Dean’s swallows, watching as Dean suckled down the contents of the bag for five minutes until it was empty. 

“Good but...I think you can get better. I think another will do for you,” said Sam, snapping his fingers. Salty liquid filled his mouth again, Dean staring at Sam wide eyed. “I don’t want you to worry about not getting your snack after all. You did such a good job, toy.”

Sam moved around behind him as Dean growled, Sam quickly pulling the plug out of Dean’s ass, examining the puffy red rim. Sam cocked his head and snapped his finger, Dean shrieking when he felt cool liquid surrounding his rim and in his ass.

“S’just lube,” said Sam, grabbing his brother’s hips and lining his cock up with his hole, Dean shaking his head and looking over his shoulder at him. Sam pushed the head of his cock against the taught skin, Dean moaning as Sam gave a chuckle. “Knew you’d be a whore for your brother’s cock.”

Sam ran his thumb around Dean’s rim, stretched around the fat head of Sam’s cock, before he slammed it inside, Dean howling as Sam bottomed out. Sam gripped Dean’s hips hard and pushed up into him, over and over again until he was hitting Dean’s useless prostate every single time, Dean crying out as Sam pushed him closer to an orgasm he’d never have.

“Fuck,” groaned Sam as he bottomed out and came again, pulsing deep into Dean. He slipped out and grabbed the plug from his back pocket, this one longer and thicker as he pushed it into Dean’s hole. It’d be a quick and dirty fuck but Sam knew it was important for Dean’s training. His hole belonged to Sam now.

Sam gave Dean’s ass a hard slap, a nice red handprint appearing on the cheek, so nice Sam gave the other one the same treatment. Sam whisked away the old, smaller toys, not that Dean would be needing them ever again. He was only going bigger in his training otherwise it would be unfair to Dean. Consistency was the only thing that was going to work.

“Toy,” said Sam, the flow in Dean’s mouth gone now, Dean squeezing his eyes shut as Sam laughed. Sam shoved his hand into his pocket and pressed the button on the remote, Dean’s eyes flashing open as he felt the plug vibrate in his ass, right up against his prostate. “I know it’s very important for us to train regularly but I have some very important business to attend to. I’ll be sure you get your snacks and are played with regularly but we may not see each other for some time. I will be back though. I promise.”

Sam gave Dean’s clamped nipples a twist each and patted his caged cock before he turned and left, leaving Dean in the light this time. He looked around, trying to fight through the pain that radiated through him when he felt the gag start to leak again, Dean letting out a sob as a new stream of cum started to pool into his mouth. He wanted to throw up but had a feeling Sam made no longer being able to do that an improvement to his body as well. His stomach felt heavy with cum and his insides felt wet, ass stretched wide around a thick, bulbous plug that was going straight to his dick that couldn’t get hard to save his life. 

Dean sucked down his “snack” as he looked down, watching the clamps on his nipples magically tighten before him, Dean screaming into the gag before it went back to the simmering pain below the surface.

Dean stared at the floor and tilted his head, spotting the mirror that was there and aimed underneath him. The plug inside of him looked huge and his balls were a deep purple.

Sam was turning him into his own personal sex toy and he had no way to stop it.


	3. Chapter 3

Dean felt delirious. He’d lost track of time after he’d tried to figure out if his Sam cum snacks were on a schedule which they certainly were not. His nipples were throbbing but the clamps were no longer on them which was a nice change of pace. The plug in his ass continued to vibrate, keeping Dean on the edge of coming over and over, in a heightened state of desperation that never ended.

Dean was losing his damn mind.

“Good morning, toy!” said Sam, slipping into the room happily, a little snap of his fingers and the vibrations stopped, the gag was gone and the obnoxiously heavy belly bulge of cum felt like it had never existed. Dean glanced down and saw a smooth stomach again, tilting his head as he saw smooth everything. “Toys don’t need hair.”

Dean tried to speak but his voice was gone after the constant sucking, jaw too tired to do anything. 

“I’m sorry I was away for three weeks. It was longer than I intended,” said Sam. Dean knew there was no way in hell it’d been three weeks. Sam was lying to fuck with him. Then again, Dean had no way to tell time down there and maybe Sam really had left him like that for that long.

Dean didn’t know why he was crying, not resisting it when Sam pressed a rough kiss to him.

“It was the first part of your training, toy,” said Sam. He smiled as he lifted up Dean’s limp cock and knelt down. “You look so much better without them.”

Dean felt Sam’s hands tickle a sensitive smooth patch of skin at his crotch, the pain soothing away after a moment.

“Fell right off,” said Sam, picking something off the ground. Dean couldn’t look, Sam sighing as he snapped his fingers and Dean felt much warmer. He was in the library, arms restrained behind his back, face down on the table and legs spread out and secured at the ankle, leaving his ass hanging off the edge. 

Sam removed the plug and slid his cock into Dean, not moving at all.

“Clench down on me,” said Sam, running a hand down Dean’s back. Dean’s ass complied, Sam smiling behind him. “You will clench your ass anytime a dick is put in you, understand toy?”

Dean nodded, voice still gone, bearing down on Sam as he grabbed Dean’s hips and fucked into him hard and dirty. His caged cock was trapped between his stomach and the table, the pressure of Sam hitting his prostate a strange one now that he was ball-less.

“You look so beautiful, toy,” said Sam, brushing his thumb over the newly bare spot of skin. “I made you sterile. Made you into the perfect bottom bitch you were always meant to be.”

Dean whimpered as his dick tried to get hard but failed, too tired to care about keeping up a tough appearance. He cried the whole time Sam fucked him and emptied a hot, messy load of come in him.

“Good toy. Good toy,” said Sam, pressing his balls up against Dean’s ass, making sure to pump every last drop of cum into Dean. “I got you a new treat for being so good.”

Dean gasped when the blunt tip of fat headed dildo pressed against his hole, ten thick inches pushing inside of him. It had to be at least three inches wide, Dean sobbing when his ass tried to expel the intrusion.

“I know. Such a bad hole for trying to get rid of your new toy. Don’t worry. It’ll stay nice and put once we get the knot in,” said Sam.

Dean didn’t have time to think before he screamed, nearly blacking out at the pain at his rim, something obnoxiously large and round shoving in his hole before it narrowed down.

“Took that four inch knot like a champ,” said Sam, tracing his finger of the puffy red rim, smearing the small amount of cum that had escaped around it. Dean thought he was getting used to the pain when he suddenly found himself sat on the edge of the table, dildo buried in his ass and legs tied to the table posts. His arms were still around his back and Sam was right in front of him, kissing the tear streaks off Dean’s face. “Remember what I said to do when you have something in your ass. Clench.”

Dean whimpered as he squeezed around the dildo, relaxing and doing it again as Sam watched him.

“You broke easier than I thought you would,” said Sam, Dean trying to look away but Sam was grabbing the penis gag and securing this one in Dean’s mouth, longer and thicker than the other two had been. Sam walked over to another table and grabbing a bottle of balm meant to cause a burning sensation, smearing it on Dean’s nipples before he reapplied the clamps. Dean cried freely now, barely making a sound as he watched Sam wipe off his hands.

Sam looked the hunter up and down, smiling at the progress Dean was making.

But there was still an important part of that training to be dealt with and Sam had grown impatient after being away from Dean for so long.

“I know losing your balls was a very hard thing for you today, toy, but it was necessary. Toys don’t come. Toys don’t get pleasure. Toys give pleasure and that is their purpose. Toys don’t deserve anything because they are worthless,” said Sam. He took Dean’s chin in hand and undid the straps on the gag, pulling it out for only a moment. “What are you?”

“Toy,” squeaked out Dean, Sam running his thumb over Dean’s lips. He didn’t dare say anything else. He just wanted the pain in his ass to go away.

“What are you?” asked Sam again.

“Toy,” breathed out Dean on a shaky breath. 

“Toys don’t get what?” asked Sam.

“To come,” said Dean, Sam forcing him to meet his gaze. “Pleasure.”

“What do toys do?” asked Sam.

“Give pleasure,” said Dean.

“Toys don’t deserve anything because they’re what?” said Sam.

“Worthless,” said Dean.

“What are you?” asked Sam.

“Toy,” said Dean, Sam smirking at the thought that that was now Dean’s default answer.

“What else are you, toy?” asked Sam.

“Worthless,” said Dean, Sam so proud of his toy for getting there on his own.

“You are such a good toy. You are worthless and worth nothing but because you have been such a well behaved toy, I’m going to give you a present,” said Sam. Dean glanced at the penis gag, Sam chuckling. “You feel empty without your gag in, toy?”

Dean nodded, not quite understanding why but the gag brought him a little bit of comfort, made him feel safe when he was owned in every sense of the word.

“I’ll give you your gag back. We’ll leave it in for a long time. We’re going to leave it in forever just maybe,” said Sam. “First you need to get your present and I want to hear a thank you when I say so.”

Dean blinked up at him and then bowed his head, Sam beaming as his toy’s natural submissive side was shining through.

“Look down, toy,” said Sam. He waited as Dean’s gaze landed on his caged cock. Sam pressed a hand over top of it and quietly said the incantation he’d memorized. It’d been very old, very dark, very messy magic, meant for torture but Sam thought it had other uses. Getting Dean to feast upon his cum hadn’t been that hard but the payoff was more than worth it.

When Sam finished, Dean watched as his cock was suddenly gone, only a bare surface there. Sam ran his fingers over the soft skin, down to where his balls had been, pleased when there was no reaction to the touch.

“Sterile, ball-less, cockless. This is how a true toy is meant to be. Say thank you for making me into a perfect toy,” said Sam.

“Thank you for making me into a perfect toy,” said Dean, staring blankly at Sam. 

“Again, what are you?” asked Sam.

“Toy,” said Dean, Sam so happy with his new toy he could burst. Sam smiled as he picked up the gag and secured it in place, chuckling when Dean went to absently sucking it.

“Let’s put you back where you belong toy,” said Sam, snapping his fingers, Dean back in the dungeon only now he was strapped down to something soft.

Soft. Dean hadn’t known soft for so long he started to cry at the padding under his chest and belly. His cock no longer hurt, balls no longer hurt. The nipple clamps dug into his buds as Dean felt the thick leather strap across his back but he smiled around his gag as he sucked. 

Dean didn’t bother to try to move his arms or hands behind his back, despite feeling a tightness all around him. It was dark but he didn’t mind it. Sam gave him something soft. He made him feel all warm and safe and his ass didn’t even hurt anymore at the monster cock that was in there.

“Toy,” said Sam in the darkness, Dean not bothering to move. “I’m guessing you’ve figured out you’re back in the playroom. We’re going to focus on training your ass. It is lubed and ready for use. I expect to see you clenching like a good toy. You live in that latex suit now. This is the last time I will speak to you. From now on, it is at you. Not that you’ll hear a word I say.”

Dean realized he couldn’t speak or hear in the next moment, his vocal muscles only allowing tiny whimpers and whines, Sam chuckling.

“That hole is going to be wrecked by the time that machine is done with you,” said Sam. Dean felt the large dildo’s knot pull on his rim quickly, popping it out and making Dean whine. The dildo pulled out until only the head was inside, harshly slamming back in, forcing the knot into Dean’s hole before thrusting back out, leaving only the head.

Sam clicked a setting on the machine so it fucked Dean steady, knot fucking him over and over, Sam smiling as the dildo must have been scraping over Dean’s prostate. It was nothing more than a tease now, a release that no longer existed.

Sam wondered how long it would be before Dean lost every trace of himself and became the perfect toy he was meant to be.


	4. Chapter 4

Sam was hard before he even walked into the dungeon. He’d strapped his toy down to the machine three days ago and offered him no reprieve. He didn’t need it. He was a toy and what it felt meant nothing. Sam wandered into the room and looked at his perfect, black and shiny wrapped human toy. There were only holes for the nose, mouth and ass. The black latex was wrapped so tight around the toy he could see the nipple clamps under the suit, Sam smiling at the smooth mound of skin where Dean’s cock and balls used to be. Sam watched the machine fuck into the toy at a brutal pace, the rim long since loose and puffy red with lube everywhere.

Sam could never have done this as a human. His abilities afforded him such things now. 

Sam stared at the dildo and watched as it changed, smirking as he pulled out his cock, the toy groaning at the larger intrusion. Sam glared at it. He wanted to break it’s mind fully and that took patience. Sam took his cock in his hand as he watched the four inch wide and thirteen inch long cock disappear into the toy’s stretched hole. It tried to wither but that only agitated Sam, starting at the dildo until it was replaced with another and the toy started to scream as best it could without a proper voice.

It could not hear and Sam made no fanfare about watching the sixteen inch cock plough into the hole. It was four inches wide but had a six inch knot, the toy howling every time it pulled out and forced it’s way back in.

Sam gripped his cock and stroked it hard and rough, ignoring the slight burn as he pumped his cock, shooting his load at the toy’s hole, the knot pushing it inside when it pushed past his rim. Sam went to the toy’s mouth and ripped out the gag, shoving his filthy cock inside. The toy cleaned it without question, working Sam back to hardness until Sam was coming deep down it’s throat. He shoved the gag back in place and eyed the toy’s hole, deciding it needed more time with the machine to work the sounds out of it.

 

Dean was vaguely aware when his ass burned anew, gaping wide around the thick intrusion. He’d thought he’d had Sam in his mouth for a moment but he couldn’t be sure of it. Dean wasn’t sure of anything anymore. He knew he was a toy meant for Sam’s pleasure. He knew he’d had some kind of plan before that but he couldn’t remember what it was. He liked it when Sam touched him, not the merciless machine that fucked him without thought, like he was an object.

Dean had a moment of clarity, remembering he was a toy. Sam didn’t want him to be Dean anymore. He wanted a toy. Toys didn’t move or scream or anything, no matter what was done to them. Little moans and whimpers would be okay. Dean just had to get his body to learn to do that.

So he thought and thought and thought until he felt the dildo in his ass get thicker and larger, until the clamps on his nipples were so tight he learned to love the hurt. Hurt was what he needed. He could be the perfect toy for Sam. He could take bigger toys. He could take whatever Sam gave him and he would do it perfectly.

Because that’s what toys were for.

 

“So,” asked Sam, walking around the bunker two months later, watching the monster cock pump in and out of the toy’s hole. “He learned to think of himself as nothing more than a toy. He gave himself the larger dildo until he no longer has a response to it. His nipples have been in chastity for just over two months ago and he is in an incredible amount of pain yet only sucks on his cock and clenches down as best he can when the dildo enters him.”

“With the anal gaping he has, I’m surprised there’s even the ability to do that,” said one of Sam’s lead demons in charge of his toy project.

“He has the ability because I gave it to him,” said Sam. He tilted his head at the toy, brushing his fingers across the nipples in the suit, getting no reaction.

“Pain just spiked,” said the demon.

“Yet no reaction. He’s almost perfect,” said Sam, nodding for the demon to leave. Sam snapped his fingers and the machine was gone, Sam smiling at the red puffy hole. It was stretched wide and thanks to Sam’s body modifications, it’d be staying that way as long as he wanted. “This’ll be your true test, toy.”

Sam pumped up his cock and sighed when he was able to put a few fingers inside the toy’s hole without touching the sides. He took a deep breath and snapped his fingers, watching the hole snap back to a normal shape and size. Sam liked a wet fuck so he made sure a litte was inside the hole already when he shoved his cock into the hole in one hard thrust.

The toy didn’t make a sound, didn’t move an inch. Sam grabbed it’s hips and thrust hard, slamming his hips over and over again into the toy, the toy clenching down like it was supposed to, nothing beyond that as Sam spilled his seed inside the toy, pumping his come deep. Sam grunted as he pulled out and grabbed a nine inch, medium girth dildo and placed it in the toy’s hole as a plug. Sam secured a latex band over and around the toy’s hips and thighs so keep it secure and tight.

Sam had to wait months before he finally worked the last traces of Dean from his toy but now he knew he was gone forever, only a perfect set of holes to be filled, used and wrecked remaining.

 

Sam was enjoying himself in the bunker’s library, he’d quite liked the place when he lived there. The beautiful wood, all of the lore books...it reminded him of his college library almost, back when things were simple.

A demon entered the library, Sam jutting up his chin.

“I need a break from the toy for the moment,” he said, waving the demon off. “Make sure it’s in use though while it waits for me.”

“That’s the thing sir. The toy...it’s gone.”


	5. Chapter 5

Dean groaned as he nearly fell into the motel wall. He was still trapped in latex, bound, and unable to see or hear but he knew the smell of a crappy motel room anywhere. He tried to take a deep breathe through his nose and calm down. Most everything was a blur, the past few months swirled together in his head as nothing more than pain, denied pleasure and the word ‘toy.’

Dean had to focus hard to get his mind not to drift back to that pliant mindset and knew if he could get out of the damn suit and restraints, he’d feel human again.

Dean knew he’d prayed, over and over and over again when Sam first caught him, until Sam had worked that out of him. Worked everything out of him.

But something had saved him from that awful place. Something had given him a bit of his clarity back. Maybe it was Cas and it was a fast in and out job so he had to ditch Dean in the safest place he could find. He didn’t exactly care at the moment as long as he could work himself free.

Dean’s legs shockingly were not bound together. At least not tightly. He was able to take a very small step before moving his other foot, legs immediately giving out at lack of use. His body screamed at him for the sudden pain but he used that, tried to get mad and stay mad. It helped him remember. He was Dean. Not a toy.

Dean knew what he was looking for, finding it after what was probably half an hour crawling around on the floor. It seemed like nothing to Dean, his internal clock was gone and he felt like maybe his patience had grown through all of this. When he hit the radiator, he fumbled to his feet to turn it out. It was hard with the mittens but thankfully he could just turn a knob before the thing started to crank out heat.

Dean knew there’d be more pain involved with burning rubber on his skin to get free but he’d dealt with worse.

Twenty minutes later Dean was shaking as the leather cuffs around his wrists finally, finally broke enough that Dean could pull his arms in front of him. His entire body ached but god, he could  _ move _ his arms again. The leather on his ankles was much easier to get rid of but Dean was having no use getting the mittens off. 

He knew they were a part of the suit so he simply had to figure out how to remove it. Dean thought for a good long moment before he touched the the back of the neck of his suit. There was some kind of leather there he was sure of and Dean leaned his head back next to the radiator. After a few minutes, a pressure he’d never noticed on his neck fell away and Dean fumbled something hot away from him. Dean reached behind him and found a small zipper that’d been hidden by the leather. He pulled on it as best he could until it stopped. He felt fresh air on the back of his neck. He was so happy he wanted to cry.

But he had to keep going for the time being.

Dean used his trapped hands as best he could, taking a deep breath as he tugged on the latex, pulling it up and down over his face, ripping small tubes in his nose out. Dean paused and had to shut his eyes, even the dark more room too bright after all that time being blind. He smiled though and started to attempt to remove the suit.

He struggled with how tight it clung to him but after an hour, he had most of the suit off his chest and arms, just fighting with removing his hands still.

He gave a few good pushes with his one hand and feet against the now slack material and yanked on his arm, his hand popping free. He flexed it and was amazed how it was working despite all that time in the suit.

Sam must really have made some changes to his body if his fingers were working just fine.

With one hand free, Dean was able to rip off the other mitten and start shimmying out of the suit. It stuck in some places but Dean didn’t care once he plucked the last on the latex off his foot. He laid back against the carpet, eyes tearing up at having finally adjusted to the light, at the felt of a scratchy carpet under him. 

Dean plucked the ear plugs out, the world suddenly so loud as he heard low traffic outside, a car door slam, a dog bark. Dean rolled and got up to his knees, figuring these last parts had to be quick and dirty.

He reached a hand to his clamped nipple and undid it, wailing into his gag which was the only reason it was still in there at all. He did the other one fast, curling in on himself for only a moment, again reminding himself that the pain would fade and his new body was made for this. He reached behind himself and found the base of a thick dildo, fingers wrapping around it and trying to tug.

His ass decided to clench down on it, trying to keep it inside. Dean pulled again, getting the same automatic response from his ass until he just yanked it out  _ hard _ , ass easing up as it was removed.

He felt...empty. So fucking empty without it. He reached up behind his head and undid the straps for the gag, pulling it out and dropping it on the floor.

“Talk…” said Dean, closing his eyes in relief that his voice was back. He was okay. He was free and he was okay again. He’d figure out how to get ahold of Sam and get his little brother back.

He certainly wasn’t anyone’s bottom bitch toy anymore either. 

Dean didn’t want to think about the fact that Sam had forced himself on him or all the things he put  _ on _ him,  _ in _ him,  _ done _ to him.

Honestly all he wanted was a hot fucking shower.

Dean slumped into the bathroom and turned on the hot water, waiting a moment as it heated up. He caught his reflection in the floor length mirror.

He looked smaller, weaker which was to be expected after being held against his will for so long. No hair below his chin and-

Dean stared at the smooth mound of skin below his stomach, lightly touching a finger to it, jerking his hand away when it felt like nothing more than touching skin. He closed his eyes. It’d just been one of Sam’s tricks. He couldn’t have actually…

Dean opened his eyes again, whimpering when the smooth flesh was still there. He rubbed his hand over his skin again. No sensation, nothing that felt good at all.

Dean sludged into the shower, hanging his head as a few tears fell. He thought it’d been fake, a trick. But the bare skin meant his cock and balls were gone.

_ Oh god. I can never come again. I can’t even use the bathroom again. _

Dean slammed his fist against the shower wall, wanting so badly to be angry, furious.

All he felt was humiliated. Sam had turned him into a fuck toy that couldn’t get off.

Dean fell back against the tile and stayed there until the water turned cold.

 

When Dean finally dried himself off, he knew it was time to stop feeling sorry for himself. Maybe he could still get something out of his new situation. He laid back on the bed, sighing into the softness before he spotted the mirror above him. He blushed at his own reflection now. 

He turned onto his stomach and reached behind him.

“I can’t believe I’m actually going to do this,” mumbled Dean. He sighed before he wiggled a finger down to run over his still open hole, puffy and red and gaping. Dean slipped a lone finger inside, trying to think of anything else until he found that soft spot inside him. He smiled into it. It was enjoyable and sharp but at least he felt  _ something _ .

Until ten minutes later and he was crying into the mattress, built  _ so close _ to an orgasm that should have long since come and gone. He felt that pressure, that need, the build of it inside of him but there was nowhere for it to go until it slowly simmered away.

Dean laid there for a long time. It wasn’t like he was hungry or thirsty. He didn’t need to use the bathroom. He could just lay there the rest of his life if he wanted. He wondered if he could die but decided he probably could if he really tried. Sam had changed him but only so he wouldn’t break under his strength.

Dean didn’t want to think about that either and rolled off the bed, looking around for some clothes but finding none. He’d have to steal some but it wasn’t anything he’d never done before.

He grabbed a towel and his ice bucket, padding outside, smiling as he saw the sun setting.

God, the lingering warmth, the breeze, they felt  _ amazing _ on his skin. He had a plan though and quickly went to go get some ice, finding a housekeeper at the last room in the place. It was easy enough to pretend he forgot his key and slip inside like a forgetful patron.

He found some boxers and a t shirt, already wearing them when the door opened and three huge guys walked in.

“Is that my shirt?” said one, Dean holding up his hands.

“Let me explain,” said Dean, two of the guys on him like that, Dean mortified at the pitiful fight he put up. He was no match at all for them. “I wasn’t trying to steal. I just need a pair of jeans please and I’m gone, I swear.”

“Looks like you were stealing to me,” said one. Dean struggled against the two guys that pinned his arms back but it was worthless. The guy that seemed to be the leader of these three walked forward and grasped Dean’s chin. Dean took a deep breath, trying to ignore that he had the same look in his eye Sam did when this all started.

“I’ll give the clothes back. Just let me leave,” said Dean.

“You can have the jeans. Keep the clothes you got on. Hell, we’ll toss in twenty bucks. You just ooze desperate boy,” he said. Dean swallowed hard. Cops were a bad idea and prison worse if this fight had been anything to show for it.

“I’m sure we can come to a deal,” said Dean shakily. The man grinned, the other two chuckling as one released Dean long enough only to removed his belt and secure it around his wrists. Dean dropped his head, trying to stay calm. He was free if they did what they wanted. He just had to do this for a little while and then he could go.

“We each get a turn with that pretty mouth of yours,” said the man in charge.

“I get my jeans, money and I can go after that?” asked Dean. The man nodded and Dean hesitantly returned one. He was knocked down to his knees, the man who’d already removed his belt stepping in front of Dean.

“You ever done this before baby?” he asked. Dean had honestly only given two blowjobs before, both forced and he’d grown accustomed to the way a cock felt in his mouth. He figured fifteen minutes and he was out of here.

“Not really,” said Dean. The man chuckled as the other two took seats on their beds, watching as the man guided his semi-hard cock to Dean’s lips. Dean opened his mouth the second the salty tip touched his lip and suckled the head in. He grew a long groan from the man, his hand resting in Dean’s hair as Dean worked the head over.

“Fuck. You suck cock like it’s your job, baby,” he said, pushing more of his cock into Dean’s mouth. It wasn’t as wide as the gag had been and the man didn’t even try to deep throat him, coming already and filling Dean’s mouth. It tasted different than Sam, more rancid but Dean was glad he had no gag reflex anymore as he worked the man’s cock until it was spent.

The man pushed Dean away when he was too sensitive, taking a step back as another stepped up.

“Might be the best warm mouth I’ve ever been in boys,” said the man that finished, Dean opening his mouth without asking, finding the man’s cock thick in his throat, sucking his cock hard.

“ _ Fuck. _ His  _ throat _ . You were born to suck cock, little slut,” said the man, delivering long and hard thrusts that had Dean squeezing around him every time. Dean felt him swell up and hollowed his cheeks, the man coming straight down his throat with a roar. He pulled out with a pant, Dean licking his lips when he was gone.

“Let’s see if you live up to the hype,” said the leader, standing as he whipped out an impressive cock, something to rival Sam’s even. The man shoved his cock into Dean’s mouth, waiting until Dean choked a little to pull back and thrust back in. Dean could feel the tears in the corners of his eyes now as the man used and abused his mouth, the man grunting and groaning, moaning what a good whore Dean was the whole damn time. When Dean thought he was about to come he pulled back and slammed his entire length inside, pulsing into Dean’s mouth and throat, fucking it as he came.

Dean swallowed it down without protest, settling back on his heels when the man pulled out and wiped his cock clean on Dean’s face. Dean panted as he stared up at him, looking at the other two men.

“Ricky, watch him. We might just have an opportunity for you to make some more money, bitch,” said the leader. Dean wanted to protest, he’d done his end of the deal and all but the two men left, leaving Dean alone with the largest of the three men.

“Never knew a guy that could suck cock like that. Your pimp teach you that?” asked Ricky. 

“Pimp? I’m not a prostitute, asshole,” said Dean, the guy walking over and slapping Dean in the face.

“You suck cock like one. Bitch,” said Ricky. Dean glared at him, ready to spit back at him when the two men came back in the room.

“You staying here?” asked the leader. “Whore, you staying at this motel?”

“No,” said Dean. “Let me-”

“Five hundred bucks if we all get a turn at that ass and we’ll even give you a ride to the bus station if you want,” he said.

“What’s your name?” asked Dean. The man chuckled.

“I’m Rusty. This is my associate Willy and you’re already antiquated with Ricky so let’s skip the pleasantries and get down to the good fucking we all know you came here for slut,” he said.

“I didn’t-” said Dean, cutting himself off when he saw Rusty hold up the penis gag. Dean whimpered at the sight of it, Rusty laughing.

“The maid told us about an interesting fella she saw. She sneaks us tips time to time. You are one kinky son of a bitch, aren’t you?” he said.

“No, I’m not. I’m a nobody,” said Dean.

“Bitch says she doesn’t have a pimp,” said Ricky. “If you do, now would be a good time to say so.”

“You fucking assholes, I’m not a whore or a prostitute or have a pimp or any of that shit. Just let me go. Now,” said Dean, glaring at the three of them.

“Good,” said Rusty with a smile. “Judging by the state you’re in, no one’s going to come looking for you either.”

Dean went wide eyed as a hand slammed over his mouth. He struggled but it was nothing once all three had their hands on him and shoved the gag back in his mouth, Dean shouting around the intrusion.

“Be a good bitch now and take it,” said Rusty. Dean felt his shirt be ripped off along with the boxers, all three staring at him and taking a step back. Hopefully they thought he was a freak and would let him go. “Holy-”

“Shit. He ain’t got no cock. Or balls,” said Willy, reaching forward to touch it and making Dean jerk back into Ricky’s hold. “There’s a tiny scar there but nothing.”

“Would you look at that?” said Rusty, rubbing his hand over the area carefully, watching Dean’s face for a reaction. “The bitch don’t feel a thing. Oh that is  _ amazing _ . Just two perfect holes.”

He reached out and pinched a nipple, Dean squirming into the pleasure pain, knowing he’d never get to feel that pleasure ever again.

“She’s just a cunt,” said Ricky, smirking against Dean’s ear, Dean trying to turn away but held still. 

“You got rid of your nasty little bits so you could be a perfect cunt for real men to fuck? Huh?” said Rusty. “You two take his ass. I got calls to make.”

Rusty left the room and Dean was hauled over to the bed and shoved face down. He felt the wet squelch of lube over his hole before a finger was roughly shoved inside and then another.

“God, she’s already prepped,” said Willy, the lube squelching again before Dean felt the fat tip of his cock press against the rim and slip inside. He screamed as he pushed in what felt like an eight inch cock and god Dean was embarrassed he knew that from feel alone now. Willy just laughed as he turned Dean over, Ricky playing with Dean’s nipples and running his hand over his bare mound, Dean whining into his gag.

“Look at this bitch. A whore for getting her titties played with and best part is she can’t even cum. Just a cunt to use,” said Ricky, Dean crying and doing his best not to as they started to laugh at him.

Sam was evil. Sam was a monster. Dean could understand why Sam would betray him and get a sick twisted pleasure out of what he did. But these men were just men and Dean thought they might just be as worse as his little brother.

Dean whimpered when he felt a hot load of cum up his ass, Ricky quickly swapping in for Willy, plowing straight through the cum and pushing it deep, Willy twisting and pulling at Dean’s nipples the whole time.

“This ass...fuck it’s like it’s fucking milking you every single time,” groaned Ricky, finger tips pressing into Dean’s hips hard.

“I know, right? No way this whore wasn’t slutting it out on the streets. Probably tried to have a real life and couldn’t quite make it. Don’t worry whore. We got the perfect place for you,” said Willy, Dean whining as his prostate was pounded again and again, the pressure of an orgasm there, Willy laughing in Dean’s face. “Keep hitting his prostate. I want to see if he can really come after all.”

“I don’t want to break it,” said Ricky, shifting his hips to comply with Willy’s test. Dean wailed and cried, both men amazed before Ricky finally came hard. They moved around and Dean felt what felt like a thick plug shoved in his ass, keeping their cum warm inside him. Dean trembled as they played with his nipples and sucked on them, arching his hips and looking for any kind of relief.

“She can’t come,” said Willy.

“Go tell boss. This is going to be the score of a lifetime.”

 

Dean wasn’t sure where he was but his penis gag had been replaced with an extra large red ball gag that stretched his lips. He had a blindfold on most of the time until someone took a picture of him and back on it went. He was moved from the motel to what smelled like the back of a bar, Dean blinking furiously when the belt around him was upgraded to leather cuffs.

Fuck. 

He was caught. 

_ Again. _

“See you around bitch,” said Rusty, his friends laughing as Dean felt another presence in the room. A new man moved around in front of him and Dean already despised him.

“You’re my new bitch. I own you. You got good looks and the way those boys tell it, you know how to take a cock at both ends. Here’s the deal. You’re spending your first week in the gloryhole. 12 hours on. 12 hours off for sleeping. The boys said they did some ‘tests’ with you. Say you’re some kind of super freak. Don’t need food or breaks or nothing. You’ll go 12 hours straight through and cum gets cleaned out before the next session. You might hear the other bitches getting breaks or going about doing other shit but you don’t get that. I bought you. I own you. As long as you’re a pair of holes, you’re good to me,” he said.

Dean closed his eyes, silently pleading with the man, nodding to someone behind him.

“Put him in the heavy usage stall and secure him. Spider gag him too. The pretty cockless bitch that can’t come is already drawing a crowd tonight.”


	6. Chapter 6

Dean tried to fight back as a spider gag was secured behind his head, forcing his mouth open. He was brought into a locked room with a padded bench, strapped down on his stomach, legs secured straight down and to a wall, his ass flush with a hole. His head and chin were maneuvered until his mouth was lined up with a hole, lips sticking through the thing, a tiny pad on the wall for Dean to rest his head against.

The plug in his ass was removed and someone probebed his ass with three fingers for a few minutes before they were satisfied.

“Have fun bitch,” said the men who’d worked him into place. Not long after they were gone, Dean heard other doors open. A cock was shoved in his mouth and started to thrust immediately into Dean’s throat, Dean trying to move away but he was strapped down too good. He moaned around the cock in his mouth when he felt one slide into his ass. It was probably the gentlest fucking he’d ever had back there and despite the fact his body was being used without his permission, Dean sort of wanted to thank that person.

It didn’t last as the guy pulled out and another cock replaced it within ten seconds, Dean swallowing down his first load of cum as the guy in his ass absolutely wrecked it.

Dean fell into a rhythm of drinking down cum and taking a load in his ass, everyone commenting how perfect he was, what a perfect dickless cocksucker he was. A perfect bitch, a perfect pussy, perfect cunt. A warm set of holes. A sloppy cum dump.

Dean felt the bulge of his belly, wondering how much time had passed before his mind started to wander, his ass clenching down on each man’s dick every time it pushed in or thrust out, Dean getting so many compliments on how well  _ trained _ his cum fucked hole was.

Dean was jello when the last man shot a load in him and he felt a plug in his ass. He heard doors open and shut, his eyes barely opening when he saw the door to his room open.

“Never seen anyone actually last 12 hours on the stand. Best goddamn toy I ever bought.”

 

Dean was dragged off the bench and taken to a room where his gag was removed and he saw how his belly bulged with cum. Someone told him how many men he’d taken but Dean was too fucked out to even hear or care. He wanted an orgasm he wasn’t getting and now the constant buzzing in his body was quiet thankfully. A pill was slipped under his tongue and Dean was brought to a bathroom, sat on the toilet and his ass felt like it let the entire contents of his body out at once. The reaction certainly wasn’t what they were expecting but Dean’s stomach was a normal size again and Dean figured it was his body’s new way of dealing with a laxative. He was pushed under a shower and told to clean, Dean taking the small bit of privacy where he could get it. 

When he was finished, he was brought to a single small room and told to bend over a bed. His hole was fingered roughly. Dean just stood there and took it, knowing he wasn’t getting past these guys, too tired to try even. When the man seemed finished, the other put on a pair of latex gloves and opened a locked drawer, squeezing some cream onto his finger. He globbed some onto Dean’s nipples, working it into the skin as he pinched and twisted them. He did so for only a minute before he applied more to his finger. He rubbed it over Dean’s hole and then pushed a big glob of it inside, shoving it deeper with his finger as it coated his walls. The man grabbed a thick plug and shoved it inside before he removed the gloves. A special chastity belt, like one a girl wore, was placed on Dean tightly and then locked, told that was how things went and if he had a problem with it, something bigger would be going up there. Dean just nodded as a cuff was attached to his ankle, the men telling Dean to rest while he could as he’d be back on the stand soon.

Dean sat down on the bed and then lay, thinking his situation was still a million times better than when he was with Sam. Of course that was easy to say when he wasn’t being mercilessly fucked by a hundred men for hours and hours.

Dean rolled over to his stomach, gasping off the bed when his nipples brushed the sheets and felt on fire. He started to feel a burning heat at his hole and in it, his nipples on fire.

“No,” said Dean, grabbing the sheets and trying to rub the cream away but it’d already soaked in. “No! Stop it! It hurts!”

Dean shouted and banged on the wall until he’d shouted himself hoarse and lay there staring at the wall, praying that when they came to get him for the stand they’d undo whatever they did to him.

He was being trained all over again.

 

Dean only got the burning capsaicin cream for three more nights before he’d been labeled a “good bitch” from his new owner. Dean didn’t fight when they took him to the stand anymore and he’d taken to offering himself to the men that ordered him around at the end of the night. It was beyond demeaning but it got him treated a bit better and after a whole night of cocks, what was a few more?

Dean got used to the constant wear and tear on his body, caught in a limbo most of the time but he had to remind himself this hell hole was still better than being Sam’s mindless fuck toy.

A toy with no thought or feeling, wrapped in latex and purely a set of holes. People often told him he was just that, a set of holes. Dean would always laugh to himself about how being strapped down in a glory hole was nothing compared to the mind fuck Sam had done to him for months.

About three weeks in, Dean was surprised to be taken to the boss’ office instead of his stand. He was naked apart from his plug and leather cuffs behind his back when he was ordered down on the nice leather chair.

Dean stared at it and decided it was better not to get in trouble and simply knelt beside it, his owner smiling when he saw how Dean reacted.

“You’re a good bitch, sweetie. A very good bitch. You’ve brought me a lot of money lately. Showed the other bitches, the free bitches, what’ll happen to them if they ever try to skimp off the top. I would keep you forever if I could. But business is business and a very wealthy man purchased you from me for all exclusivity to that ass and mouth. It was a deal I couldn’t pass up. He’s been made aware of what a cum slut you are. I know you’d appreciate that,” he said with a smile. “Our business is done. If he ever gives you your freedom back and you’re looking for a quick buck, come find me.”


	7. Chapter 7

Dean was shaking as he knelt in a cold hard basement, arms behind him, a ball gag in his mouth, a spreader bar keeping his thighs wide as he sat there, impaled on a thirteen inch, four inch wide cock. Dean knew his knew owner was a huge pain play guy as soon as he saw him but when he realized what Dean was capable of, he’d made it his mission to try and break Dean. Literally.

“Another inch, another hour,” said Yates, Dean’s very wealthy owner from his lush chair in a corner of the play room. Dean whined when he saw Yates hit the remote, the dildo inside of him attached to a strong metal rod in the floor that Yates had more than assured Dean could fully support Dean’s weight and then some. The dildo was now at a point where Dean’ knees were barely touching the floor anymore, his back straight as a board to try and keep his weight off the magnificent beast inside him. “Still fighting it I see. You won’t have a choice in 59 minutes.”

59 minutes later Dean watched in horror as Yates hit the button, the dildo rising another inch, Dean’s knees off the floor as he fully sat on the thing. He screamed into his gag, Yates walking over and examining Dean, smirking horribly at him.

“You really can’t be broken. Fascinating,” he said, hitting the remote so the dildo pulled away and started to pound up into Dean. Dean shrieked and shook for hours as Yates watched, never once touching his cock. Finally he stopped the pounding and pulled out the dildo, Dean slumping down to the floor.

Yates picked up a syringe from close by, half of Dean hoping it was something that would kill him at this point. Instead he rolled Dean over to his back and stuck the syringe into Dean’s left nipple and then his right. Yates leaned back as Dean stared up at him, smiling at him.

“You have a very well trained ass. A very well trained mouth. Your nipples though seem to have been neglected. We will work on that,” said Yates. Dean already felt something strange happening to them, Yates chuckling as he picked up a pair of clamps like the kind Sam had used and attached them too tightly to the buds, a deep red coloring flushing them. “It should not take long for the drugs to take effect.”

Dean could only lie there as Yates lubed up a large dildo, the one Dean had been afraid of the second he was brought down there two days ago. It had a round thing almost at the bottom Dean knew was supposed to be the knot. It was a gigantic sixteen inches long, probably three wide with a six inch knot. Yates looked a bit evil as he positioned it into Dean, forcing him to take the knot and stretch his rim taught. Dean howled when he felt the knot slip in, Yates patting him on the head. He saw the two tubes that connected to the dildo, Dean hating how his ass was already squeezing the knot like he was some kind of trained slut.

“This will keep us entertained until those cherry red titties are ready,” said Yates. Dean cocked his head as Yates hit two buttons. Dean felt the knot inside of him start to expand, Dean screaming as his body tried to rid it from itself. He also felt a hot splash of something, something like  _ cum _ filling him up. Dean barely stopped to see the tube was connected to two giant tanks full of it on the side of the room.

Dean cried as he was impaled, his ass squeezing the knot, shocked when it backed off for a moment and he got a fresh squirt of cum. Dean looked at Yates as he did it again, Yates chuckling at him.

“Figuring it out are we? That is a very special dildo and a very special knot. The sensors will know when you milk the knot with your cunt and will reward you with cum and a more manageable sized knot. If you stop squeezing, the knot gets larger. If you keep milking that knot with your little cunt like you’re supposed to, it won’t hurt, understand?”

Dean nodded and shut his eyes, clenching around the fake knot, milking it, hard and fast a few times as he got the knot down to only three or so inches. He could keep up with it at that point and was used to something that girthy, starting to get used to the fact he got a load of cum every time his body forced it into him. The knot still kept the cum in him though and Dean knew even with his newly found magical body, even he couldn’t store that much cum in himself without bursting.

Yates grabbed another pair of tubes and brought them over in front of Dean. Dean’s nipples felt heavy and full when Yates removed the clamps. Yates chuckled as he squeezed Dean’s nipple, twisting and pinching them both until little white buds formed on the top.

Dean looked up at Yates who only smiled.

“The drugs I gave you will force you to lactate. You don’t have any milk though and while I originally was going to give you something to make you do that, I figured why not have you milk the cum out of your body? As you milk that knot with your cunt, it’ll fill you up. The drugs will direct it into your ducts and it’ll…” said Yates, squeezing a bud hard until it felt like it had popped open and cum flowed freely from it. He gave the other nipple the same treatment, Dean shouting as Yates held up the little tubes from before. “We don’t want you making a mess so these pumps will direct all the cum your titties milk out down the tube, back into the tank where it’ll warm up before it goes right back into that ass for knotting and milking again. I’m very excited to get to try this one out.”

Dean tried to move away as Yates attached the tubes to his nipples, the things stuck on as he watched the cum flow from the tips and down the tube, back to the tank. Dean milked the knot again and watched as more cum was milked out of his nipples.

“The suction is merely for the cum to get back in the tank once it’s released from the nipple. It won’t pull any out. Your milking of the knot will make sure the cum gets up to these perfect titties,” said Yates. “We’ll train you up just right.”

Dean screamed at him when he started to move away, forgetting to keep up with his clenching for a moment as the knot grew larger, forcing Dean to milk it hard and fast to get it smaller, his nipples oozing and oozing cum.

“I have some appointments out of town. I know you don’t require things a normal person would but I will leave the light on for you so you can watch how beautifully you milk cum,” he said. “I’ll return in three weeks.”

Dean was bawling before Yates even got to the door.

 

Dean knew he was losing it when he started to play games with himself, seeing how much cum milk he could get out of himself at once, figuring out knot sizes and timing. It gave him something to do at least so he wouldn’t go insane.

As if he weren’t already insane.

“There’s my beautiful milking machine,” said Yates, smiling at Dean as he clenched around the knot and more milk came from him. “I’ve been watching you while I was away through the cameras. You never even slept. You are an incredible find.”

Dean stared at him as he kept up his current rhythm, before Yates went over to his machine and flicked it off, the knotting dildo deflating some, the suction tubes falling off. Yates removed them and cleaned Dean up before he injected something into his nipples again. This time the effect was almost immediate. Dean was lactating, a thin white liquid that dribbled down his chest. Yates took a nipple into his mouth and sucked on it, milking Dean and swallowing it down as it was dried up. He did the same to the other nipple, Yates wiping off the excess with the back of his hand when he’d finished.

“Did you like all of the cum in you, making you warm inside?” asked Yates.

Dean nodded without thinking. Cum wasn’t so bad after all. Insanely gross and messy and at least it made his nipples feel a little good.

“How about we put all the cum back in you and then it can leak out of your titties for days?” said Yates. Dean simply nodded again. Maybe he’d finally get to sleep at least without having to concentrate on something in his ass.

Dean was not prepared for the enema going up his ass or the intense steady pressure of it. Yates knew what he was doing obviously but Dean had never felt anything like this before, Yates telling him what a good cunt he was as he forced some of the cum and then more into Dean, so much Dean felt it in his stomach. Yates plugged up Dean’s hole tight so there was no leaking. He removed the spreader bar and bound Dean’s ankles and thighs together with bands. He slipped a band over Dean’s chest so it was just below Dean’s nipples and then another above, keeping Dean more than secure. Yates injected each nipple with a syringe this time before he positioned Dean into a sitting position against the wall and pulled a strap across his chest, one across his stomach, one on the floor across his thighs and another across his ankles.

Dean felt as wrapped up as when he was in that latex suit. Yates moved Dean’s head and strapped one across his forehead, forcing Dean to stare ahead. There was a camera and television right in front of him, focused on his nipples. He was going to have a front row show to his nipples leaking cum for days.

_ Kill me now. _

“Now the injections I gave you this time are a little different. You will lactate the cum far more slowly but at a steady flow. Your nipples will also have a...reaction to the cum now. It will cause pain and pain will slow the lactation rate. It won’t stop it but it will slow it. The less in pain you can feel, the faster this is over with. I suspect it’ll take a week but you may surprise me. This is all part of your training, cunt,” said Yates. He twisted Dean’s nipples painfully until Dean felt the cum produce from them and start to flow down and fire shot through the sharp peaks. Dean howled as the rate certainly slowed but didn’t stop, Dean sobbing into his ball gag, watching his chest try to heave on the television but nowhere to go, his nipples lactating cum at an agonizingly slow rate.

 

It took a week and half for his nipples to stop lactating, Dean strapped down in a sticky pile of dried cum, registering pain in his nipples but no longer bothering to react.

Yates must have liked that one because he did it  _ again _ , Dean getting himself to stop lactating in just six days this time. Yates decided Dean needed pretty much constant milking, whether he was milking a knot or getting his titties drained, Dean was always wet with aching nipples.

Three months in with Yates, Dean realized he eagerly looked forward to having his nipples abused and tormented by his capturer. Maybe because Yates was rich and could afford to do things that men at the motel or gloryhole couldn’t. Whatever it was, Dean found he was turning into a milk slut.

“Cunt,” said Yates when he came into the playroom one day, holding up a set of new syringes that made Dean tremble with excitement. “I have a very special treat for you today.”

Dean tried to be as still as possible as Yates injected one syringe into his nipple and then another. He gave the other nipple the same treatment before he went to Dean’s ass and pulled out the dildo he’d spent the night sitting on. He injected something into the rim of Dean’s anus and then carefully found Dean’s prostate and injected something into it.

“Would you like to know what I did?” asked Yates, Dean nodding eagerly. He could feel his bottom suddenly get wet, Dean looking down as slickness leaked from his hole. His nipples felt wet as well, gorgeous white milk dripping from them. “Your nipples will now permanently lactate as I know you enjoy that. Your useless prostate has found a purpose after all. Your body still has the ability to  _ think _ it’s aroused so whenever it doesn, it’ll lactate heavily and during other periods, moderately. I also provided a slicking feature to your anus. You will self lubricate now like a cunt would. You will squirt from your nipples like a cunt would but will derive no pleasure. You are literally a cunt for the fucking now. How does this make you feel, cunt?”

Dean couldn’t hide the fact that his nipples were lactating hard, milk pouring down his chest, slick running down his thighs.

He was a good little cunt.

 

Yates had to go out of town again but made sure to attached Dean to the milking machine, Dean even getting a bigger dildo this time so he could really strength up his cunt muscles according to Yates. Yates was so proud to watch him eagerly ride the knotting dildo, milking his own milk up into his body and then having it sucked out through his nipples.

Dean rode that dick hard and long even though he couldn’t orgasm, he could see the fruits of his labor, getting rewarded with bigger loads every time until his nipples were leaking like they were niagara falls. 

Dean hoped Yates left him like this for a month.

 

Dean turned into a full on cockslut after his month alone with the milk machine and knew that some little thing he’d been grasping onto was gone. Only he couldn’t be bothered to remember what it was. Yates had trouble keeping up with the cunt’s eagerness at times, having to use fucking machines in that sweet cunt just to keep it satisfied. 

“Cunt,” said Yates, Dean turning his head one day from where he was being brutally pounded by a monstrous dildo on a fucking machine. “I’m letting you go. I can no longer satisfy this incredible need for sex you have. You derive no pleasure from it.”

Dean shook his head at Yates as he injected his nipples with something and then his prostate.

“You will no longer lactate. You will still slick since I figure that’s something you’ll need given your condition,” said Yates as he removed Dean from his bindings.

Dean couldn’t understand what he did wrong the whole way to the bus station, Yates dropping him off with clothes, a bag and a few things inside to get by. Dean cried as he got on a bus and went the only place he knew someone would still want him.


	8. Chapter 8

Dean knocked on the bunker door and was surprised when it opened freely. His ass was wet and nothing he’d managed to shove up there made him feel whole. He jogged down the stairs and looked around, the lights on but there was no sign of anything.

“Sammy?” Dean called quietly, looking around. “Sammy, please. Take me back. Please take me back Sammy.”

“I’m surprised to see you here,” said Sam, appearing from the library, sat in his old favorite chair from the looks of it. Dean dropped his bag and ran over to give Sam a hug as he stood, sobbing into Sam’s chest. “Dean.”

“Sorry I left. Sorry I ran away, Sammy. I want you Sammy. Want you always Sammy. Sammy loves me. Loves his cunt. Toy. I mean toy. You love your toy. I can be your toy again. Be a good toy, Sammy,” said Dean between sobs, Sam grabbing Dean’s arms so he had to stand back. “Please just take me back.”

“You’ve been gone a very long time, Dean,” said Sam. Dean shook his head and dropped his pants, pulling off his clothes before he bent over one of the tables.

“Fuck me, Sammy. Fuck your toy, please,” begged Dean. Sam gave him a small nod and stepped up behind him, not even shoving his pants down before his cock was out and he was fucking into Dean. Dean fucked back onto it every step of the way. Sam’s hands on his skin, his cock in his cunt, Sam biting possessively at the back of Dean’s neck. 

This was where Dean belonged, with his Sammy.

“Fuck my cunt, please. Fill it up, Sammy,” moaned Dean, Sam thrusting hard as he leaned over Dean, emptying a load into Dean’s ass, picking up the plug from Dean’s coat pocket and shoving it back inside. Sam grabbed Dean’s arm and righted him, Dean staring up at Sam before he leaned down and kissed him.

It was the first soft kiss he’d ever gotten from Sam.

“You came home, Dean and that’s all that matters,” said Sam. Dean titled his head at Sam.

“Toy?” Dean asked, Sam shaking his head. “Cunt? Bitch? Whore?”

“No. Dean,” said Sam, Dean crying again. “Why are you doing that?”

“You don’t want me. No one wants me. No one ever did,” said Dean, crying all over himself when Sam put a hand under his chin.

“I did. I always did. Dean, you were never alone in all this. Never. The past year has been about breaking you, yes. But breaking you out of being the  _ old Dean _ . Part of that was becoming a toy and a whore and bitch and cunt. But now you’re the  _ new Dean _ . The Dean that will cry in front of me, speaks openly and loves me the way he was always afraid to. This is what I was building towards, building  _ us _ towards. I love you Dean. I always have. I did all of this for us,” said Sam.

“Love me?” asked Dean, Sam nodding. Dean threw his arms around Sam and hugged him so tight, slick leaking down the back of his thighs as Sam chuckled.

“Yes, I ove you, Dean,” said Sam, kissing Dean, the smile on his face so big it was a wonder Dean’s cheeks didn’t burst. “You forgive me for doing all of this?”

“What’s to forgive? My brother loves me,” said Dean, smiling against Sam’s cheek before he gave him a kiss. He pulled back quickly, Sam catching his arms.

“You can kiss me, Dean. It’s okay,” said Sam.

“I won’t get in trouble?” asked Dean.

“There’s no more in trouble,” said Sam, taking Dean’s hand. “Let me show you.”

Sam guided Dean around the bunker and back to the dungeon, chuckling a little when Dean clung to Sam harder. He pushed open the door and showed it still had the padded bench and a table full of toys but the room was warmer now, the lighting softer.

“This can be our playroom when you’re up to it again. No more hunting Dean, no more badness. The only things you’ll have are love from now on,” said Sam.

“Okay,” said Dean quietly, wrapping his arms around one of Sam’s. “Can I give you a blow job?”

“Randy little thing aren’t you,” teased Sam. “Maybe after lunch, baby.”

“Baby?” asked Dean worriedly. “Like with diapers and pacifiers?”

“No, no, Dean,” said Sam with a laugh, leading him back out to the hall. “It was a pet name, a sign of affection.”

“Puppy play?” asked Dean, Sam rolling his eyes. “...Kitty play?”

“It has nothing to do with sex. It means I love you and I’m going to take care of you. Like when we were kids and you called me kiddo,” said Sam. “Only we’re big now so I should get my own pet name.”

“Sweetheart?” asked Dean, Sam nodding.

“That’s a real good one,” said Sam, walking with Dean back towards the kitchen. Dean saw a delicious looking burger on a plate as he stepped inside, giving Sam a smile. “Dig in.”

Dean dropped to his knees and started to undo Sam’s belt, worriedly glancing up at Sam when he moved away.

“I’m doing everything wrong,” said Dean, tears in his eyes again. Sam shushed him as he knelt down, running a hand through Dean’s hair. “You said dig in...I thought you wanted me to be a cockwarmer while you ate.”

“You can warm my cock, baby, but only when I ask you to, when you really want to, and certainly not right now. The burger is for you. There’s pie too,” said Sam.

“But food…” said Dean.

“The minute you came back to me and I knew you were mine forever, my Dean forever, I gave you everything back. No more big mean dildos ever again. They’ll hurt your insides,” said Sam. 

“This isn’t a trick?” Dean breathed out. “Y-You can hurt me if it makes you happy.”

“It doesn’t,” said Sam harshly. “I’ll have rough sex with you. I might punish you when you disobey with a hard spanking. I might make you do things like have you wear clamps or a plug or whatever for a few hours but I will never hurt you like I had to before. We had to get the real you out, Dean.”

“I’m sorry for not believing you,” said Dean, burrowing his head in Sam’s neck, Sam shushing him.

“No more tears, baby,” said Sam, wiping off his face. “Eat your food before it gets cold.”

Sam helped Dean to his feet and Dean made a note to be extra good about his clenching the next time he had sex with Sam. Dean took a seat at the counter and hesitantly held up the burger, taking a small bite. It tasted like heaven and he alternated between that, the pie and his beer, Sam taking the food away at the first sign of a stomach ache.

“You’re not used to eating. Take it slow, Dean,” said Sam. Dean sat patiently as Sam cleaned up and assured him he could do it, Sam eventually turning around to see Dean giving him a smile. “Yes, Dean?”

“Blowjob now?” asked Dean.

“Would that make you happy?” asked Sam.

“What would make you happy?” asked Dean.

“If you answered me honestly,” said Sam.

“...In my cunt,” said Dean.

“Cum for that hungry cunt it is then,” said Sam, Dean moving to drop to his pants when Sam caught his arm and led them to his old bedroom, new bedroom really, a large king size bed in the middle of it that Sam pulled Dean down onto. 

Sam messily undressed until Dean was pawing at him to go faster. Sam pinned Dean’s wrist to the bed and stared down at Dean, using his powers to remove Dean’s plug. He lined himself up and eased inside an inch at a time, watching Dean’s face contort happily at being stuffed full.

“Love you, Dean,” murmured Sam, kissing Dean gently as he delivered long and hard pointed thrusts that were driving into Dean’s prostate every single time. Dean didn’t even flinch, the idea of seeking his own pleasure a distant memory. Being the best at giving pleasure and making sure whoever had been owning him throughout the year got to be on the receiving end of that...that was was how Dean got pleasure now.

Sam snapped his hips hard and drove up into Dean, filling Dean with his seed, hot sticky cum filling Dean up and mixing with Sam’s earlier spendings. He pulled out and replaced the plug before Dean could ask. Dean seemed happy with a fresh load of cum in his plugged hole and Sam decided that Dean would be staying full from now on. Thanks to his slick he now produced, removal for lube replacement wasn’t necessary, only bathroom trips and even those Sam could clear up with a snap of his fingers for Dean if he was in the mood.

“Love you so much, Sammy,” said Dean, snuggling into Sam’s side, Sam running a finger down to Dean’s nipples. “Do you want to milk them?”

“I will make you an offer. I can make your nipples extra sensitive and so you can come again from a nipple orgasm,” said Sam, Dean’s eyes flashing open. “Or I can make your prostate extra sensitive so it will feel so good when we have sex, like you’re about to come, but you will never orgasm ever again. I’ll even milk your prostate but nothing will happen. You’ll be denied release. Once you chose, I’ll never undo it. Or you choose neither and I’ll never bring this up again.”

“Prostate,” said Dean without missing a beat. 

“Are you sure? I’m offering you the chance to orgasm again with the nipple option. If you go prostate, sex’ll only make that denied release worse,” said Sam.

“Prostate, please,” said Dean with a smile. “I like when you pound my cunt and I can’t cum.”

“Why’s that?” asked Sam, flicking his wrist before he started to toy with the plug so it pressed and rubbed against Dean’s now always sensitive prostate.

“...Like right now, if I could come, all I’d want is to be able to do that. But since I can’t, I have to take it and melt into how owned and helpless I am and I know that my Sammy is the one that I belong to. I can focus on pleasuring you and I don’t have control anymore and I don’t have to worry anymore because I have you,” said Dean happily.

“I made you into the perfect little sub and you’re too in love with me to even realize how fucked up this is,” said Sam, cupping Dean’s cheek as he tilted his head. “I turned you into a cock loving slut that can’t go more than an hour without a fresh load in his always lubed up cunt. You suck dick like it’s candy, ride cock like a pro, you aren’t happy with your nipples unless they send sparks of pain through you...you’re so fucking perfect now Dean you don’t even care what I did to you. I fucking broke you,” said Sam.

“I’m perfect?” beamed Dean, Sam chuckling before he kissed Dean.

“My perfect Dean. I’m gonna keep you like this  _ forever _ . Us in the bunker, you can fix up the car again, I can get back to my reading and whenever I need that cunt of yours, it’ll be right there for me, won’t it?” asked Sam.

“Always,” said Dean, nuzzling into Sam. “Can I ask for something?”

“Of course, Dean,” said Sam.

“Can I sleep with a dildo in my cunt I can’t take out? I liked that at the gloryhole. I think,” said Dean. Sam nodded and removed Dean’s plug, sliding a slender nine inch long didlo into the warm wet heat of Dean’s ass, cum and slick around it as Sam used a little of his powers to make sure nothing was lost and the dildo would stay put in there all night no matter what Dean or his body did. “Thanks Sammy. I like to sleep all full.”

“You want your nipple clamps on too?” asked Sam. “I won’t make them too hard.”

Dean arched his back in offering, Sam not bothering to move as the clamps found themselves on Dean’s nipples, Dean sighing softly at the feeling of being clamped and stuffed. Sam watched for a while as Dean drifted off to sleep naturally, the first real sleep Dean had had in a year. He was surprised how easily he did so with the clamps and didlo inside of him, even more so when Dean rolled over and everything shifted.

Sam was so proud of him at having that level of control over his body, even in an unconscious state. 

Sam had originally meant to make Dean his fuck toy and nothing more, to leave him in the latex suit for the rest of time. But a part of him missed  _ Dean _ . Missed his brother, seeing his face, seeing the unconditional love. Sam knew letting Dean escape only to be ‘caught’ by progressively worse “people”, all of whom were on his training team and were to look well after Dean, was the only solution. The time at the gloryhole had trained Dean’s ass to take a human cock far better than the dildos ever had. One day they’d left him there an entire 24 hours and told him it was his usual 12. He took over 200 cocks that day, over 140 in his ass alone. 

He loved sucking cock more than anything after the stint there and his ass was clenching involuntarily, on instinct at that point. But Yates stepped everything up. Dean’s sense of time had been horribly screwed up. Yates told him he was gone for a month when really it was three. God, Sam watched a Dean that couldn’t sleep, something Dean never questioned, rode and milked a cock, had his titties get milked, for three months straight. Sam jerked off so many times it hurt. He had no idea how Dean had pushed through the pain to find the joy in doing the best he could to please Yates.

Sam knew it was because he broke Dean, broke up parts of him that couldn’t be put back together. But Sam considered those the bad parts. The self worth issues, esteem problems, weight of the world on his shoulders...now this new Dean knew his place and had none of that. He was Sam’s and Sammy loved him. Sam knew Dean would always see himself as beneath Sam, not true equals but that was how it was supposed to be. Sam had a lot of plans for Dean’s ass or as Dean affectionately referred to it, his “cunt” and Sam had no qualms about doing every filthy thing that came to mind with it. But this new Dean loved Sam so openly and so much that Sam couldn’t bear the thought of putting Dean back in the latex suit, not for more than a play session here or there and he had a feeling that was long down the road. 

No, he’d broken Dean into what he wanted him. There was no need to break what little remained.

Sam was surprised when Dean chose the option of his prostate over an orgasm, a part of him having wanted to have an excuse to ring painful orgasm after orgasm from Dean. But no orgasms were better after all. Dean was compliant and submissive now and focused on Sam and Sam couldn’t have been more in love with the man sleeping next to him if he tried.

 

“Sammy,” said Dean the next morning, gently nudging Sam awake. He stretched and saw a pair of concerned green eyes staring back. “I have to use the bathroom.”

“The dildo will come out when you pull it out in the bathroom,” said Sam with a yawn.

“I have to pee. How do I…” said Dean.

“You pee out of your cunt,” said Sam with a soft smile, ruffling Dean’s hair. “Better go before you wet yourself.”

Dean hopped out of bed and was gone a few minutes, sighing as he climbed back into bed with Sam. Sam grabbed his hips and rolled him to straddled his torso, ordering him to ride him. Dean arched his back and clenched his cunt like a porn star, Sam playing with the nipple clamps before he took them off and started to pinch the sensitive buds, Dean slamming down and ripping Sam’s orgasm from him.

“Fuck,” groaned Sam, cuming harder than he had laying on his back in...ever, quickly reaching into the nightstand drawer. “Clench.”

Dean was a pro at it, lifting off of Sam’s cock and lowering back down on the thick plug.

“A nice load of cum to start the day,” said Sam, Dean laying back next to him. Sam splayed his hands on Dean’s stomach, letting them trace down to where his cock and balls used to be. “You used to have a big cock and balls like me.”

Sam teased the skin with one hand as he jerked his cock back to life with the other, Dean watching both of Sam’s hands work until Sam was at full staff again. Sam sat up and knelt between Dean’s legs, spreading them wide until the tip of his cock was against the smooth skin. Sam jerked himself off as Dean watched, soon another hot load of cum shooting of of Sam’s cock and over the skin, Sam took a finger and swiped it around, chuckling to himself.

“You look so perfect like this Dean,” said Sam. Dean’s cheeks flushed a bright pink under the praise, Sam kissing him for a few minutes before he told him to get ready for the day.

Sam expected Dean to come to the kitchen after his shower but when he heard nothing of the sort, he went in search for him, finding Dean sat on the bench in the playroom.

“What are you doing sweet boy? You need breakfast,” said Sam. Sam watched as his head dropped, Dean gripping his bare thighs. “Do want me to play with you while we eat?”

Dean nodded and only moved off the bench when Sam held out a hand for him, guiding him to the kitchen where Sam pulled out his cock and had Dean climb on top of it while they ate. Sam was sweating by the time they’d finished, Dean working his cock while they made idle chit chat about the bunker and how Sammy had made the world a better place in the years he was gone. 

“Sammy?” said Dean when he was pulled off of Sam’s lap and into the empty spot next to him. 

“Why don’t I finish in your mouth?” asked Sam, Dean moving to the floor, sucking Sam’s pulsing cock into his mouth. Seconds later Sam’s orgams hit, Dean drinking him down until Sam was forced to push him away. “You like your breakfast treat?”

“Uh huh,” said Dean, Sam chuckling when Dean got to shaky feet. 

“Today we’re going to get into a routine since I know that’ll help you,” said Sam.

“Okay,” said Dean, a small waver to his voice.

“Everyday when we wake up, I’ll fuck you. After you’ll take a shower and meet me in here for breakfast. When we finish, I’ll give you a breakfast treat,” said Sam.

“I like that,” said Dean with a relaxed smile.

“Good. After breakfast, we’ll watch some television or I’ll read. You’ll be a cockwarmer while I do that,” said Sam.

“Then what?” asked Dean. Sam kissed him as he stood up and started to pick up the plates.

“It’s a surprise. Just like the one waiting for you on our bed. I’d like you to wear it while keep me warm,” said Sam. Dean nodded and practically jogged from the room, Sam humming as he washed off the dirty dishes and settled himself into the back of the library where a couch and TV area had been set up. Sam knew Dean would find him eventually but still waited to turn on the movie until Dean showed up.

Dean’s face was red and his eyes watery as he slid down to the floor on the knee pad there, Sam grabbing his chin before Dean could get his mouth on him.

“I thought we talked about you crying,” said Sam.

“Sorry, Sammy,” said Dean, looking away. Sam narrowed his eyes and got off the couch, walking behind Dean and sighing.

“Dean. Please tell me you did not put that large of a plug in you without any lubrication,” said Sam. Dean shrugged and Sam snapped his fingers, Dean jerking when he was face down on the couch and his hole was empty. “I healed you.”

“Thank you, Sammy,” whimpered Dean quietly. “I’m sorry. I’m so bad at everything. I can’t follow your instructions.”

“You’re not in trouble Dean. You’ve never put in a plug yourself, have you?” asked Sam. Dean tried to think about that fact before he nodded. “Your training isn’t done yet.”

“But my cunt makes slick,” said Dean.

“It does but putting even very big things in you requires more. You need to make sure you are always properly lubricated,” said Sam.

“Couldn’t you make my cunt do that all the time?” asked Dean.

“I could but I want you do that. You’ll get real good at lubing your toys and plugs up and putting lube in your hole. Cum works like lube too but you’re all empty from your shower so next time, you use lube or I’ll give you a spanking for it,” said Sam.

“C-Can you write this all down for me?” asked Dean. Sam smiled and kissed his shoulder, snapping his fingers as he earned a groan from Dean. A wet plug was snug between his cheeks, Sam guiding him back down to the floor.

“There’s a little cheat sheet on your nightstand for you now,” said Sam.

“Thank you, Sammy. I won’t mess up again,” said Dean, happily leaning forward to suck Sam’s soft cock into his mouth, resting his head on Sam’s thigh.

“I know you won’t Dean.”

 

It took two days before Sam introduced Dean to his afternoon routine. Dean sobbed the whole time Sam put a penis gag in his mouth, attached the nipple clamps to his buds and was led by the arm to the playroom. But he never fought and Sam knew at that point he never had to worry about Dean ever trying to leave him.

Dean sniffled when Sam put him on the padded bench on his stomach and secured his wrists and ankles, laying there as Sam removed his plug.

“Hush, baby boy. Don’t you trust me?” asked Sam. Dean nodded his head as best he could, Sam running a hand up and down Dean’s back. “You need to get used to continuous use again.”

Sam moved a dildo to the edge of Dean’s hole, pressing only half of the head inside, wanting Dean’s rim to catch and get a nice good fucking as the head slipped out each time.

“One hour,” said Sam, turning the machine on. Dean started to tense up at the intrusion but sighed into his gag when he saw Sam come around to sit in front of him with a book. Dean blinked at him as his ass was steadily pounded, Sam giving Dean a friendly smile. “When it’s done, I’ll take a turn and then we can go out for dinner, how’s that sound?”

Dean closed his eyes and gave as pleased a hum he could, drifting away to the feeling of being fucked by a machine.

This was where he belonged.


	9. Chapter 9

**Notes for the Chapter:**

> A/N: The end of this chapter is very dark and includes "death" but not really. It'll be explained in the next chapter :)

Sam could feel his dark side slipping back into focus when he drove them home from dinner that evening. It’d gone wonderfully and Dean acted very well in public all things considered. He’d broken him but Dean was able to order for himself and hold a conversation as well as the old one had. Sam loved him in his suit and had removed Dean’s tie the second they were in the car and tied it around his wrists, fisting the other end like a lead with a hand as he drove. Dean was comfortable with it and sat there with a smile.

That was when he started thinking he was too sweet to Dean. The old Dean would come back around if he kept letting Dean have freedoms.

Sam drove until they found an abandoned barn near the bunker, Sam pulling Dean inside by the tie. He yanked on it hard and Dean exhaled a small gasp, Sam shoving him to the ground and kicking aside some hay, finding a tether ring in the floor meant to keep the bales in place. Sam secured the free end of the tie to it and literally  _ tore _ Dean’s suit and clothing off, Dean quietly looking up at Sam the whole time.

Sam scowled at him, Dean bowing his head and pressing it to the floor, arching his back and presenting his ass. Sam was this close to snapping his fingers and forcing a dildo the size of his fist in Dean’s unprepared hole when Dean turned his head up at him.

All he saw was love. Confusion but love. If he did this, he’d break this new Dean, turn him into a shell that feared his touch. Sam could be as rough as he wanted, as twisted as he wanted without all the formalities. There were positives to a warm set of holes to fuck.

But this Dean nuzzled into him in bed. This Dean held his hand and couldn’t go long without touching Sam. This Dean was so soft and pliant.

He could always find another toy. But he only had one Dean.

Sam knelt down behind Dean and only undid his belt and zipper before sliding into Dean’s wet hole. Dean had prepped himself, Sam so proud of him for actually being ready, so mad at himself for almost hurting Dean for no good reason.

His balls slapped against Dean’s ass and he saw the fingertips he’d left behind on Dean’s skin as he came, hastily moving away and out of the barn before Dean had even taken a breath. When Sam had finally calmed down, Dean was still in position, dried come on the back of his thighs, some still leaking from his hole lazily.

“Dean,” said Sam, Dean lifting his head up.

“Did I do it wrong?” he asked quietly. Sam shook his head, cupping Dean’s cheek. “Sammy?”

“There is something in me that is wrong, Dean. Something that wanted to hurt you tonight. I told you I wouldn’t do that and I know you trust me with you but I don’t know if I trust myself, you see,” said Sam.

“Hurt me, please,” said Dean, Sam shaking his head. “If that’s what you want.”

“No,” said Sam. “I need to clear my head, figure out what path I want to take, what path you’ll go down with me. I think for us both now in that regard.”

“Samm-” said Dean before he was cut off, Sam removing his own tie and gagging Dean, tears prickling in Dean’s eyes. 

“I’ll be back within the hour.”

 

“Dean,” said Sam, Dean whipping his head around, turning around on his butt as Sam approached him. He pulled down the gag and untied Dean’s hands, pressing a finger to his lips. He didn’t speak as he drove them both back to the bunker, Dean keeping his hands in his lap, shivering a bit in the cool car, dried tears all over his cheeks. Sam sent him to the showers and then bed, Dean’s poor head spinning and spinning with uncertainty but he followed the orders given to him.

Sam was waiting for him when Dean entered the room, startled at first until Dean took a spot next to him.

“Dean, I-”

Dean leaned over and kissed Sam, giving him a smile when he pulled back. Sam returned it, kissing Dean’s nose, blush spreading across his cheeks.

“I’m sorry for confusing you. This has all been very strange. I’ve let others train you when it seems I could have done with some training myself,” said Sam.

“No, you’re perfect, Sammy,” said Dean.

“You will have two hours every afternoon to yourself. I will travel elsewhere to take out my agressions in a healthy manner. You’ll be alone to do as you please,” said Sam.

“I can do whatever I want?” asked Dean. Sam nodded and gave him a smile.

“Whatever you want. You can watch TV or read or go for a walk or work on your car...anything you want, baby,” said Sam.

“Can I play with myself?” asked Dean.

“You can do that but remember, this’ll be after I’ve played with you all morning and lunch and afternoon. You might want a break before we play in the evening again,” said Sam.

“Okay,” said Dean. “I know just what I want to do.”

“What’s that?” asked Sam.

“You can find out tomorrow if that’s okay,” said Dean, a small blush on his cheeks.

“Yeah. It’s okay with me, Dean.”

 

Sam felt a million times better when he got home from Hell the next day. Taking everything out on some low level demons for a few hours made him feel good and only left behind the soft fuzzy feelings he had for Dean. Sam knew he’d come home a few minutes early so he could see what Dean was up to but this was certainly not at the top of his list.

Dean was in the toy room, lazily on the bench, peacefully asleep.

“If that’s not the cutest and most adorable…” said Sam, seeing the folded up piece of paper next to Dean’s still body. His very, very still and cool to the touch, body. He picked it up, a short breath escaping him.

_ Sammy, _

_ You died a long time ago. The real you did. This version of you, he broke me. He broke me pretty good but you know what? I still remembered Sam. My Sam. My Sam loved me. I loved him. This one, whatever the fuck you are, you don’t. You don’t even know what love is, psycho. You would have been better off leaving me a mindless fucktoy. Toys don’t think but you gave me freedom to fuck with me or break me or some shit but it backfired buddy. I held on tight to the little scraps of me that managed to survive. It was so easy to play the broken in love thing you created. I was that thing, almost. You destroyed almost everything. But I remembered who I really was, that this is beyond wrong and this is the opposite of love. I knew I had to play along and play along until you left me alone, not tied down, for the first time in ever. I thought I’d have to wait a lot longer to be honest. You fucked up, Sam. _

_ It was just pills. I took every damn pill we had in this place. It’s not gonna hurt and even if it does, who cares. You lost. You don’t get me. You don’t own me.  _

_ You’re gonna find me in your precious playroom.  _

_ Rot in Hell, bastard. _


	10. Chapter 10

**Notes for the Chapter:**

> A/N: FYI, the series will start to get a bit different than previous parts here on out :)

“Dean! Dean!” shouted Sam, Dean’s body fucking  _ killing _ him, aching everywhere. He was on cement, large hands pushing on him. Dean blinked open a hazy eye, Sam in front of him, touching his shoulder, his face.

“No, Sammy,” Dean whined, trying to roll away, feeling his wrists rub against rope. No. He took the pills. He was dead. He was dead. Sam couldn’t get him anymore. Dean felt his bound hands and felt his lip start to tremble. “N-No!”

“S’okay, Dean. You’re back,” said Sam, reaching behind Dean to untie him. Sam helped him sit up groggily. Dean tried to shift away but Sam pulled him into a hug. That was when Dean spotted the dead djin on the ground behind Sam. “I got him Dean. You’re okay. It was just a dream.”

Dean swallowed hard, looking around.

“Is this real?” asked Dean quietly. Sam stared at him before he scrunched up his face and slapped Dean, Dean groaning. “Fuck dude!”

Dean shook out his head, panting a few times as the heavy fog suddenly left his body. He was certainly still a bit off from it all but he was Dean fucking Winchester. He wasn’t anybody’s fucktoy and Sam had never hurt him. He hugged Sam far too tight but Sam didn’t seem to mind. It was his Sammy. His real, soft, sweet, loving Sammy. He sighed in relief before quickly reaching his cut up hands to his belt and shoving his hand underneath.

“It’s back!” said Dean with a smile, lifting up his boxers, staring down at his cock and balls, Sam looking the other direction.

“If you’re done looking at your junk, let’s get you out of here and someplace safe, alright?”

 

“Stop squirming,” said Sam, dabbing Dean’s cut on his cheek carefully with alcohol in their motel room. It was just like Dean remembered. Sam said he’d only been missing for a day.

“Stop manhandling me, bitch,” said Dean.

“Jerk,” said Sam, sticking a bandage over it, running his thumb over Dean’s lips. Dean froze, Sam pulling his hand away before he cleaned his cut lip, Dean sighing that that was all he wanted. “What happened? In the djin world?”

“Nothing,” said Dean.

“You look scared of me, of making me mad,” said Sam. Dean was about to protest but Sam rolled his eyes, and Dean felt his lip quiver on instinct. Sam gave him a soft smile, Dean closing his eyes. “I’m sorry. I know that djin stuff is rough.”

“It’s alright, Sammy,” said Dean.

“Why are you so afraid? Did I...was I dead?” he asked. 

“Whatever that was in there, he wasn’t the real Sammy and I wasn’t…” said Dean, closing his eyes. “What am I to you?”

“My brother?” answered Sam. Dean stared at him and gave him a nod, Dean throwing his arms around him. “Were we not brothers there?”

“I can’t talk about it Sammy,” said Dean, pulling back after a minute, giving Sam a smile. “I’ll be okay. I promise. I just need to shake this off.”

“You’re starting to scare me, dude,” said Sam.

“No more scaring, Sammy. No more.”

 

Dean had never been more content to be hunting on the road with his brother, to head home to the bunker and have it be a place that felt safe, actually safe now that he knew the difference. After more burgers, booze and brotherly bonding time than he could handle though, Dean got a different kind of itch.

One that made his cock stir and Dean in need of a good fuck.

It was three weeks after he was “back” that Dean had sex with the pretty brunette at the diner in the back of Baby after a hunt. When he finally came, he blacked out it felt so good. The sex was great and he kept up with finding a hookup in every town they had cases in. 

Until Dean found himself fingering his hole open as he jerked himself off one night. It just felt nice, to be filled up with something. He’d never done it before his strange djin experience. Only one woman he’d been with had stuck the tip of her finger up there during a blow job but he didn’t remember it feeling like this. Curious, yes. Tried it? No way. At least not until now.

Dean started to tease his new partners into playing with his hole but only some took the bait and the few that did, Dean hated how small their fingers felt. 

Two weeks into his new experiment, he bought a few toys online and some lube, nothing big leagues but he thought it might scratch his new itch.

Dean didn’t even get the dildo in halfway before he blew his load the first time. He waited until he was calm again to work the rest inside, whining a little when it bottomed out. It was nothing like the feeling he remembered but there’d always been a bit of pain with that. Now, he could find out what it really felt like to cum from a dick in his ass and enjoy it.

 

Turns out it was so great and Dean got so fucking loud when his orgasm hit him, Sam got concerned and nearly burst down the door, Dean scrambling under the covers just before the thing flung open.

“Dude!” said Dean, waving Sam out. “Personal space.”

“I thought…” said Sam, spotting the bottle of lube on the nightstand drawer, Dean grateful everything else was tucked away. “Were you jerking off?”

“It’s my room. I ain’t bothering nobody,” said Dean. Sam rolled his eyes and immediately left, pulling the door shut.

Two more weeks went by before Sam started to eye Dean suspiciously at the breakfast table.

“Okay, you must be doing  _ something _ new in there because you were never that loud before,” said Sam. “Even when you were fourteen and found out what your dick was for the first time.”

“It’s disturbing that you know how old I was when I started...” said Dean, shaking his head. “If I jerk off too loud for you, you can just get a motel room or noise cancelling headphones or something.”

“No, I just...what are you doing? It sounds like you’re having a good time in there,” said Sam.

“I’m jerking myself off. Nothing interesting about it.”

 

“Fuck,” groaned Dean in the shower a few days later, nearly coming before he even managed to turn on the shower head. He was off the beginner plug and was getting used to walking around with the thicker one. He’d prepped before the shower so it wouldn’t hurt because he’d had enough of that for a lifetime. It was like his ass couldn’t get enough since he’d been back, enjoying the feeling of being stuffed full more often than he liked to admit. Dean had spent the day before at the bunker wearing a small plug and was hoping he could pull it off again.

Until Dean wandered back to his room after his shower, Sam crossing his arms as he came inside and sat on his bed.

“What are you doing?” asked Dean, holding his towel around himself.

“I’m just letting you know that I’m going to stay in town for a few days. Give you some ‘me’ time,” said Sam.

“Okay…” said Dean, eyeing Sam as he stood up. He patted Dean’s ass with a laugh as he walked past, Dean clenching around the plug and gasping. “Dick.”

“Don’t you mean ass?” said Sam, pointing to Dean’s nightstand, his smaller plug sitting on top.

“That’s not-”

“Dude. I don’t care. You think you’re the  _ only _ one that’s played with a dude’s ass before?” said Sam.

“I’ve never done…” said Dean, staring at Sam. “When…”

“I was in college. I tried it once, decided I liked to top better,” said Sam.

“You’ve  _ fucked _ a dude? Wait, you’ve been fucked  _ by _ a dude?” asked Dean.

“Yes,” said Sam. “Like I said, it was college. I wanted to know what it felt like.”

“What’s it feel like?” asked Dean.

“You ever come in a girl’s ass?” asked Sam. “No condom?”

“...No,” said Dean.

“Well a girl’s ass is great but a guys? It takes a pounding like a chick’s never could,” said Sam. “Just something to think about.”

“Why are we talking about sex?” asked Dean.

“You’ve been weird since the djin thing and I don’t know what you saw over there but if you saw something that made you want to fuck all the time or get fucked or like guys-”

“Watch it,” said Dean.

“All I’m saying is it’s cool,” said Sam. “Just tone down being such a moany bitch.”

“Great. Now get out of my room.”

 

Dean made it two hours into his long weekend alone to wonder what it would be like to get fucked by a guy. For real. To feel his cum inside him, fill him up. To have a live and hot dick pounding into him. 

“Fucking shit,” said Dean, pulling out his plug, tossing it aside to clean later and grabbing his coat.

He went to Rory’s a few streets off of main a few towns over. Dean had never been before but he knew it’s reputation and was surprised to find it a bit grungier than the regular bars he frequented in Lebanon. He took a seat at the end of the bar and ordered a shot and a beer, the shot going down fast before he played idly with the cool bottle in his hands. He looked around for a moment, plenty of guys there so it wasn’t dead but it wasn’t crowded either, enough space for everyone to find their own little corner to hide away in. Dean saw a few guys on the smaller side and was a little astounded to realize he was one of them. He figured most of these boys farmed or did hard work for a living. Dean liked that already. Better odds he could try bottoming.

A guy sat down at a stool a few down from Dean, ordering the same kind of beer Dean had but he didn’t pay him any attention. Dean knew how to pick up women and knew guys were attracted to him. He’d even had to turn a few down before. This guy was decently good looking, a little older than Dean, bigger arms and probably a few inches on him too.

Tonight was go big or go home.

“Sorry, Hale, he got the last of it. Bourbon?” said the bartender. Hale nodded, giving Dean a smirk.

“Should have gotten here sooner,” he said. Dean gave him a smirk back and nodded, sipping on the drink, letting his mouth on the rim of the bottle speak for him. “You new in town?”

“Not from around here. Just passing through,” said Dean. Hale and the bartender chuckled a little, Hale waving the bartender off.

“No offense but you do realize this is a gay bar, right? Ain’t gonna find no sweet little thing to take back to your truck or motel room,” said Hale.

“Ain’t look for a sweet little thing,” said Dean, looking Hale up and down, going back to his drink.

“What are you looking for?” asked Hale, giving Dean a smile that said he’d done this a million times.

“Someone who can handle me,” said Dean with a shrug.

“Is that so,” said Hale, leaning back in his seat. “You got a name?”

“Dean,” said Dean, giving Hale a smile.

“Since you are the prettiest fella I’ve ever seen in here, I am definitely not giving any of these other guys a chance at you,” said Hale. “Even if you are a virgin.”

“I’m not-”

“Dean,” said Hale with a smile. “You’ve been hard the second we started talking. I know what you want. First time is a big deal and it’s completely not a big deal. If we go out that door together, it ain’t gonna be sweet kisses and cuddling in the sheets though.”

“Maybe I had you wrong. You might be too sweet for me, Hale,” said Dean, slapping down some money and standing up. Hale put a hand on his chest when he tried to go past, Dean instantly stopping. “You clean?”

“I am,” he said. “You?”

“Yeah, because I really want you to cum in my ass tonight.”

 

Dean barely remembered how he got to the motel room, Hale pushing and tearing and shoving at Dean’s clothes until Dean was naked and on the floor, sucking Hale’s thick cock into his mouth. Dean moaned around it as Hale pulled his shirt off, carding his fingers through Dean’s hair.

“You’ve never done this before?” asked Hale, pulling Dean off with a pop, Dean shaking his head. “You’re a natural, kid.”

“Uh, thanks,” said Dean, feeling a little awkward before Hale pulled him to his feet and tugged him back onto the bed. Hale tore off his own clothes while Dean sucked in a breath he didn’t release. The guy was average, smaller than Dean but he didn’t care. Hale kissed him hard, grabbing Dean’s wrists and pinning them down. Dean groaned into it, Hale pistoning his hips to slide their cocks together.

Dean relaxed as Hale started to kiss his way down Dean’s chest, swirling his tongue around one of his nipples, Dean arching his back.

“Baby boy likes that. Remember that for your next fuck, kid,” said Hale, rubbing the other bud with his fingers. He teased but didn’t twist or pull. Dean almost asked him to before Hale sat back on his knees and flipped Dean onto his stomach. He put his hands on Dean’s ass and spread his cheeks, laughing quietly. “You’re dripping back here, Dean. Almost like you were looking to get fucked tonight.”

“Hale,” groaned Dean, Hale teasing the tip of a finger inside his puckered hole. “Hale!”

“I’ll let that slide since this is your first time and all,” said Hale, pushing one, two, then three fingers in Dean’s hole, covered in the lube Dean had doused himself with before they slid out and something round and blunt pressed against his hole. 

Dean let out the longest moan of his life as Hale bottomed out in one smooth thrust, letting his hips press flush against Dean’s ass. Hale ran a soothing hand down his back. Dean shivered into it, whole body trembling. 

“Shh,” said Hale soothingly, Dean glad he’d found someone that wasn’t all bite and was a little gentle with him. It was so much different than the dildo though, so much better and it had a rush of fake memories of being used come rushing back to him. “Let me know when you’re ready.”

Dean got his breathing back under control, giving Hale a nod after a minute.

“Still want me to wreck that ass?” he asked.

“Fuck me raw,” said Dean over his shoulder with a smirk.

“You got it, Dean,” he said. Hale pulled out and slammed back inside, Dean yelping as he hit his prostate on the first try. Hale’s thrusts fell into a quick and hard rhythm, Dean clutching at the sheets as pleasure shot through him, his cock trapped between his stomach and the bed aching for a release. “Should tell you...only way you’re gonna get off...is on my cock.”

“S’not gonna be a problem,” gritted out Dean, Hale chuckling as Dean’s body started to tense. Hale pulled himself out of Dean and he whined at the loss, Hale pushing him aside.

“Earn it,” said Hale with a dark smile, laying back on the bed. Dean dipped his head down to Hale’s cock, his strong hand catching his chin. “Ride me.”

Dean moved to straddle Hale’s lap, Hale smacking his ass when he faced away from him. Dean swallowed and turned around, face flush as he grabbed Hale’s cock and lined himself up with it. He lowered himself down almost all the way when Hale thrust his hips up and nailed Dean’s prostate again, Dean practically falling forward onto him. Hale dropped his hips and waited as Dean settled down on top of him, resting his hands on Dean’s thighs.

“Ride, Dean,” he said again. Dean braced himself as he lifted himself up and impaled himself back down on the thick cock splitting him open, slamming down onto it faster and faster each time until Dean was trembling, poor cock weeping pre-cum.

“Please,” whined Dean. Hale held his wrists together so he wouldn’t touch his cock, Dean starting to feel his pleasure building up. “Please let me come.”

“Ride it on home, Dean,” was all Hale said, Dean pushing himself harder and harder until he felt Hale’s hands on his hips helping him, squeezing him, bruising him, a swell of Hale’s cock and then he was cumming.

It was hot and wet and sticky and Dean shot his load all over Hale’s chest from that feeling alone. He rode Hale through both of their orgams, shaking when he came down, Hale lifting Dean off of him. Dean was too fucked out to move as Hale got up, wiped himself off and started to get dressed.

“Thanks,” breathed out Dean with a small nod.

“Thanks for letting me be the one to break in that ass. Once you get a little more experience, come find me at the bar again. I can really show you some stuff,” he said, slipping on his shoes and leaving. Dean threw an arm over his face, smiling as hot cum leaked out of his hole.

He was  _ so _ doing that again.


	11. Chapter 11

**Summary for the Chapter:**

> Dean has a bad night and Sam finds out what happened to him in the djin world, leading them to a new part of their relationship...

**Two Weeks Later**

Dean was in need of some quick cash for parts for Baby and more importantly, a good fucking. He took the pictures he needed to and had prepared himself as best he could for this.

This was going to earn him a thousand bucks tonight. 

This was also going to happen whether he liked it or not.

“You the bitch?” asked a guy that looked like the bar owner as Dean walked in the place. “D?”

“That must make you TJ,” said Dean, shaking the man’s hand as he showed him through to the back. “I just checked my account and saw my half was deposited.”

“You’ll get the other half the end of the night. Flat fee. Anything extra, I keep,” he said.

“I’m just here for a grand and fuck,” said Dean.

“You’re in for a whole lot of fuck’s,” said TJ, showing Dean to a room where he could keep his clothes, smirking when Dean stepped back out completely naked aside from a simple cock cage. “You know the whole get up...it makes for good pictures, it does. But in that room, nobody’s gonna know if you come or not.”

“Yeah they will. Advertise that I can’t. The men fucking me will know I can’t. It’ll be the night of their fucking lives to have a bitch strapped down that can’t come and is only a cumdump for them,” said Dean.

“You’re gonna be on the heavy usage stand four hours, no breaks. You can go that long?” he asked.

“I guess I’ll have to,” said Dean cockily. TJ nodded, giving Dean a smirk.

“How much to rent your ass out to private patrons?” he asked.

“Not in that kind of business. You want a fuck, do it while I’m on the stand,” said Dean.

“You’re the most respectable bitch I’ve ever met, D,” said TJ as he laughed. “You and me might have the start of something beautiful here.”

“Just get me on the stand. My ass is already ready,” said Dean, TJ nodding. 

“You want a spider gag for your mouth? Gonna get hard to keep it open that long from what I’ve heard,” he said. Dean gave a nod, TJ and one of his men leading Dean into a back stall. Dean slipped the gag on and secured it behind his head, lips and mouth forced open, before he gave the guy a thumbs up. Dean grabbed the giant bottle of lube in the stall and squirted some up his ass, knowing he’d need it. When he was ready, he climbed onto the bench and moved his cock so it wouldn’t be too painful. He didn’t really need the money but he figured a glory hole was a good way to push himself and get his ass and mouth some much needed attention.

The orgasm denial wasn’t something he thought he’d ever want to try but he’d researched it and it was perfectly safe. HIs balls might be blue and his ass might be sore but that was what he was hoping for.

They strapped him down and Dean felt his ass flush with a hole, mouth flush with a hole and TJ chuckled at him. 

“You good?” asked TJ. Dean nodded as best he could in the position. “See you in four hours, D.”

They weren’t out of the room more than a minute before Dean heard both stall doors opening, a cock roughly shoved in his mouth and one in his ass, both men pining after their orgasms and caring nothing for Dean.

Dean felt himself tense up immediately, trying to repel the cock in his throat or the one in his ass, too much fear coming back to him.

This was too much, it was stupid to ask for this, to want this.

Dean was forced to swallow down the man’s cum, trying to ask for release but his words were unintelligible. He felt the cock in his ass shove into him hard, spilling cum thick and deep. Tears leaked from the corner of Dean’s eyes when another cock was back in his mouth. His cock already ached from being unable to get hard. He jerked against the restraints but he’d already gotten half of his money and that was part of the deal. He wasn’t getting out.

He shouted around the cock in his mouth that he wanted it to stop but it was too late, a warm fat cock already sliding back into his used hole, pushing through the cum as Dean sobbed. 

 

Four hours later, Dean was too tired to care about anything anymore, quickly taking the rest of his money and a quick shower before he was on the road, driving the hour back to the bunker, crying silently as his ass burned and throat felt raw. He was hoping Sam wouldn’t be home when he got back but there the big lug was, catching Dean puffy eyed as he walked down the stairs as normally as he could.

“Dean,” said Sam, grabbing his shoulder before Dean could make it back to his room. Dean shook away and tried to move away again, Sam grabbing his arms and pushing him back against the wall.

Dean couldn’t believe he started crying again, in front of Sam of all people. Sam just looked at him, Dean only meeting his eyes for a minute before he pulled him into a big hug.

“I gotcha, Dean. I gotcha.”

 

“So...we gonna talk about last night?” asked Sam, walking into Dean’s room the next morning. Dean hadn’t left it aside from taking his third shower of the day and Sam was getting tired of Dean brushing him off in the hall. All he wanted was to just stay curled up in bed forever. “Or what happened in that djin world that you won’t talk about?”

“I’m a freak,” said Dean, trying to pull his covers back over his head but Sam stopped him. “Sam.”

“Did someone hurt you last night? Not in the fist fight kind of way either,” said Sam. Dean rolled his eyes and sat up in bed, glaring at Sam.

“No. Your massive freak of a brother got pounded at both ends on purpose because he’s a  _ freak _ and I know it wasn’t real over there but my head is so messed up,” said Dean, shutting his eyes.

“You’re not a freak,” said Sam, moving to sit on Dean’s bed, taking one of Dean’s arms and holding up his bruised wrist. “This doesn’t bother me or what you do with your sex life. Having you come home like that does. Whatever you did last night wasn’t healthy or safe.”

“I was the bitch in a gloryhole,” said Dean dryly. “I freaked but couldn’t stop it.”

“Fuck, Dean. That’s...” said Sam. Dean squeezed his eyes shut. “I’m sorry.”

“And it’s nothing compared to what you did to me in that djin world,” said Dean with a sad smile. Sam pulled back and gave Dean space to sit up properly, Dean crawling out from under his covers.“You, a twisted soulless version of you, made me your own little sex toy. You broke my body, made me junkless, thoughtless, broke me down so I was just a toy wrapped up in your little latex suit in horrible pain all the time but I never could get away, just took it so you wouldn’t dream up new horrors for me. Then I got free but you let me go only so I could get caught again, only so you could have me kidnapped and raped and sold and abused and made it so I couldn’t sleep or eat or drink and was literally a living fuck toy until you broke my head and I started to think that’s what I was again. I was something to fuck and get fucked and that’s all I was there for and it actually made me kind of happy in my fucked up broken head. Until my owner abandoned me and I was so lost I went back to you, williningly, because at least I could pleasure you. That Sam...he tried to be sweet to me when I got back, saying I was the Dean he always wanted. The Dean that cried whenever he thought he screwed up, the Dean that needed Sam more than life. I was his personal little fuck toy with a clingy personality and he thought that was love. Until he started to break me even more and I woke up here again and I don’t know how to deal with what he did to me because it wasn’t real but it  _ feels _ like it was.”

Sam sat in silence, Dean pretty sure he never in a million years was expecting him to say that. After a moment Sam finally let go of Dean’s arm, resting his hand on Dean’s and lacing it together with Dean’s. Dean looked down at it and then at Sam who was staring at the wall, streams of tears down his face too.

“Sammy?” asked Dean quietly.

“I didn’t tell you but...when I found you like that with the djin, I thought you were dead. You looked dead. I’m pretty sure you were right on the edge of it. And I begged and pleaded and howled because I love you and it’s not fair I didn’t tell you,” said Sam. “It took you so long to wake up, De.”

“I know you love me, Sammy,” said Dean softly.

“Not like that, Dean. I love you,” said Sam, turning to face him, face so afraid of Dean. “It’s wrong and sick and I’m sorry. I’m the freak, not you. I know you’re hurting right now and I’ll go away forever if you want me to but I can help you or try to at least. I know it wasn’t real but the trauma is and I can help you with it if you let me. I’m so sorry. I’m so sorry that other me hurt you. You are not a toy. This version of you is the greatest thing in the universe and I’m so, so fucking sorry you went through that.”

Dean stared at Sam for a moment before he leaned in fast and kissed Sam, Sam sucking in a breath but remaining still, Dean moving his lips slowly, teasingly. Sam returned the touch, both of them working to find a small rhythm before Dean pulled back.

“You don’t scare me, Sammy, not this version and you don’t have to be afraid of me either. I don’t think you’re wrong” said Dean. Sam blinked at him, watching the soft smile on Dean’s face.

“But I’m in love with you,” said Sam. “I...I’ve been in love with you for years, Dean. Years.”

“Sam. I know what the wrong kind of love is. It wasn’t real in that world but it felt real and you are the opposite of wrong, Sammy,” said Dean, resting his forehead against his brothers. “We’ll take this real slow, so we can both ease into it.”

“You…” said Sam. “You don’t have to love me just because-”

“Shut up,” said Dean, Sam’s jaw snapping shut. “Kiss me. We both know you like to top anyways apparently.”

After a very long but sweet kiss from Sam, he forced Dean to go back to bed and get some rest, promising he’d have a nice pie all ready for him by lunchtime. Dean didn’t sleep much but did finally get dressed and at least ordered the parts for Baby he’d gone through that hellish night for.

He liked sex with guys. It was fun and dirty and rough. He still liked it with girls but he liked it with men too. It was a bit late to try and deny that at this point.

Sam...it was wrong but it wasn’t. It was wrong on a number of levels but their entire lives had been wrong in a way. There would be no other person who could possibly understand Dean, what he’d been through, no one to understand Sam either.

Frankly, Dean didn’t trust anyone else enough to help him feel better after everything that’d happened either. Sam felt safe, like it was okay maybe to let Sam help him through it. No, he knew it was okay. But this was big and it wasn’t going to be fixed overnight.

“Morning,” mumbled Dean, padding into the kitchen where a fresh pie was cooling on the counter. Dean headed straight for it and Sam frowned, Dean throwing him back a stink eye. “I’m hungry.”

“I made you a sandwich,” said Sam, nodding towards the fridge. Dean pulled it out and hopped up on the counter, eating it quietly, watching Sam clean up a few things before he came to a stop in front of him, both of them at even eye level. Dean swallowed, staring at Sam, watching his little brother’s eyes dart around his face.

“What?” asked Dean. Sam shrugged and shook his head. “Don’t act all weird because we kissed.”

There. It was out in the open and for some reason, that didn’t seem to be what was bothering Sam.

“You have a bruise on your cheeks,” said Sam, gently tapping one side then the other. Dean closed his eyes, remembering his face being forced against the hole, cheeks smashed against the wall. Sam’s fingers fell away, his presence gone for a few minutes, Dean trying to get a hold of himself.

Something cool smeared across his cheek and his eyes flew open, Sam standing there with a soft face. He held up a finger dabbed with some kind of cream and went back to lightly smearing it over Dean’s skin on the one side and then the other.

“That’ll help,” said Sam. Dean nodded and finished the rest of his sandwich while Sam washed up, his baby brother keeping an eye on him. Dean gripped the countertop, Sam stepping in front of him again. “Don’t freak out on me.”

“Don’t freak out on what-” said Dean before Sam leaned in and kissed him. Dean barely had the time to register it was happening before Sam moved back and rested his forehead to Dean’s.

“Now that you’ve had time to think about this, if you changed your mind-”

“I was probably going to hell anyways,” said Dean. Sam shook his head, moving Dean’s with it. “Yeah, I was.”

“No, Dean. You’re not,” said Sam. Dean gave a small nod, a smile appearing on Dean’s face. “I don’t want you to think I’m taking advantage of you or this situation.”

“You think you can weasel out of this?” teased Dean. “I knew you always had the hots for big brother.”

Sam blushed and looked at the ground, Dean smiling as he put a finger under Sam’s chin, urging him to look up.

“I’m pretty sure I knew you were into guys too before you did. Judgement free zone,” said Dean. “Bet you still hook up with guys.”

“Used to hook up with guys,” said Sam. “Haven’t for a while. It didn’t feel right.”

“How long is a while?” asked Dean.

“Since the djin case. You’ve been off. A part of me hoped...hoped you felt that way too,” said Sam with a laugh. “I sound like a teenage girl.”

“You got hair like a teenage girl,” said Dean. Sam rolled his eyes but Dean caught his wrist, keeping Sam close. “We take this slow, alright? I mean, the fact that I’m in love with my brother is not the strangest part about this is saying something.”

“Okay. Of course. But I have a condition too,” said Sam.

“Shoot.”

“You don’t have sex with strangers anymore and you especially never do something like last night again. You’re with me, you’re with me,” said Sam.

“Okay, Sammy. I’m not quite ready for you to jump my bones but yeah, I can do that. You too,” he said.

“Okay.”

“Okay.”

“Okay,” said Sam gently, bumping his nose against Dean’s. Dean took a shaky breath, smiling when Sam pulled him into a warm embrace. He was safe again. He’d always been safe with Sam. Dean nuzzled his head into Sam’s shoulder, his brother’s arms tightening around him. “I love you, Dean.”

“I love you, too,” said Dean quietly.

“Let’s take it easy the next few days, alright?”


End file.
